Tetrabutylammonium Fluoride → (+/-)-2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-ylmethanol

HRID 13921Notes

Reaction equation

C([Si]([O:8][CH2:9][CH:10]1[O:14][C:13]2[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=3[CH:21]=[CH:22][C:12]=2[CH2:11]1)(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[O:14]1[CH:10]([CH2:9][OH:8])[CH2:11][C:12]2[CH:22]=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:13]1=2

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 68584251(+/-)-Tert-butyl(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethoxy)dimethylsilane

Product 1

HCID 68583650(+/-)-2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-ylmethanolYield 67%

Procedure

Treatment of (±)-tert-butyl(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethoxy)dimethylsilane (4.38 g; 0.014 mol) with tetrabutylammonium fluoride (16.5 mL, 1.0 M solution in tetrahydrofuran) generally according to the procedure described for Intermediate 6 afforded 1.9 g (67%) of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethanol as a colorless oil. Rf=0.12 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C13H16O2.0.1H2O: C, 75.77; H, 7.92. Found: C, 75.77; H, 7.93.

Sources & evidence

ORD record: ord-66a801491d97443db731da9ab0bb101d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728155B2

Reaction notes

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