Next Article in Journal
1-(4-Hydroxy-3-methoxyphenyl)-4-methyl-3-pentanone
Previous Article in Journal
(±)-1-(4-Hydroxy-3-methoxyphenyl)-3-butanol
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

(±)-7-methoxy-2-methyl-1-oxaspiro[4,5]deca-6,9-diene-8-one

University of Northern British Columbia, Department of Chemistry, 3333 University Way, Prince George, British Columbia, Canada, V2N 4Z9
Molbank 2003, 2003(2), M316; https://doi.org/10.3390/M316
Submission received: 7 July 2002 / Accepted: 15 October 2002 / Published: 30 March 2003
Molbank 2003 m316 i001
The discussion and purpose for the synthesis of this compound has been reported elsewhere [1]. To a cold (0°C) solution of (±)-1-(4-hydroxy-3-methoxyphenyl)-3-butanol (106 mg, 0.54 mmol) in acetone (10 mL) was added in one portion Pb(OAc)4 (655 mg, 1.5 mmol, 2.8 eq). The resulting orange mixture was stirred at 0°C for 2 h. The precipitate was filtered through celite and ethylene glycol (5 drops) was added. The solution was stirred at room temperature for 20 h and filtered through celite. The solvent was evaporated in vacuo to afford a racemic mixture of diastereomers (58/42 ratio). Chromatography on silica gel (20% EtOAc/hexanes) afforded a mixture of diastereoisomers as a colorless oil (65 mg, 62%). Spectroscopic data were obtained from the diastereomeric mixture.
IR (neat) cm-1: 1682 (CO), 1675 (CO).
1H-NMR (CDCl3) d: Major: 1.35 (d, 3H, J=6.1 Hz, CH3), 1.79 (m, 1H, H-3a), 2.17 (m, 3H, H-3b, H-4), 3.68 (s, 3H, OCH3), 4.38 (m, 1H, H-2), 5.75 (d, 1H, J=2.7 Hz, H-6), 6.13 (d, 1H, J=10.0 Hz, H-9), 6.80 (dd, 1H, J=2.7, 10.0 Hz, H-10); Minor: 1.37 (d, 3H, J=6.1 Hz, CH3), 1.79 (m, 1H, H-3a), 2.17 (m, 3H, H-3b, H-4), 3.69 (s, 3H, OCH3), 4.38 (m, 1H, H-2), 5.70 (d, 1H, J=2.7 Hz, H-6), 6.14 (d, 1H, J=10.0 Hz, H-9), 6.86 (dd, 1H, J=2.7, 10.0 Hz, H-10).
13C-nmr (CDCl3) d: Major: 21.6 (CH3), 34.2 (C-3), 38.1 (C-4), 54.9 (OCH3), 76.7 (C-5), 79.6 (C-2), 117.3 (C-6), 125.9 (C-9), 149.8 (C-7), 151.3 (C-10), 181.7 (CO); Minor: 21.5 (CH3), 34.0 (C-3), 37.8 (C-4), 54.9 (OCH3), 76.8 (C-5), 79.6 (C-2), 117.8 (C-6), 125.9 (C-9), 149.8 (C-7), 150.7 (C-10), 181.7 (CO).
MS m/e (rel %): Major: 194 [M+] (100), 179 (34), 166 (29), 151 (61), 139 (33), 123 (33), 111 (44), 85 (73); Minor: 194 [M+] (100), 177 (8), 153 (85), 147 (16), 124 (11).
Anal. calc. for C11H14O3: C 68.01, H 7.27; found: C 67.99 , H 7.52.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowlegment

The author is thankful for the financial support provided by the University of Northern British Columbia.

References

  1. Plourde, G.L. Tetrahedron Letters 2002, 43, 3597–3599.

Share and Cite

MDPI and ACS Style

Plourde, G.L. (±)-7-methoxy-2-methyl-1-oxaspiro[4,5]deca-6,9-diene-8-one. Molbank 2003, 2003, M316. https://doi.org/10.3390/M316

AMA Style

Plourde GL. (±)-7-methoxy-2-methyl-1-oxaspiro[4,5]deca-6,9-diene-8-one. Molbank. 2003; 2003(2):M316. https://doi.org/10.3390/M316

Chicago/Turabian Style

Plourde, Guy L. 2003. "(±)-7-methoxy-2-methyl-1-oxaspiro[4,5]deca-6,9-diene-8-one" Molbank 2003, no. 2: M316. https://doi.org/10.3390/M316

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop