Tetrabutylammonium Fluoride → (2,3-Dihydronaphtho[1,2-b]furan-2-yl)methanol
Reaction equation
C([Si]([O:8][CH2:9][CH:10]1[O:14][C:13]2[C:15]3[C:20]([CH:21]=[CH:22][C:12]=2[CH2:11]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)(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[C:15]([C:13]1=2)=[CH:16][CH:17]=[CH:18][CH:19]=3Participants
Procedure
Treatment of (±)-tert-butyl(2,3-dihydronaphtho[1,2-b]furan-2-ylmethoxy)dimethylsilane (2.70 g; 8.59 mmol) with tetrabutylammonium fluoride (9.4 mL, 1.0 M solution in tetrahydrofuran) generally according to the procedure described for Intermediate 6 gave (±)-2,3-dihydronaphtho[1,2-b]furan-2-ylmethanol. Treatment of the alcohol with p-toluenesulfonyl chloride (1.64 g, 8.59 mmol), 4-(dimethylamino)pyridine (0.105 g, 0.86 mmol), and triethylamine (1.67 g, 12.89 mmol) generally according to the procedure described for Intermediate 14 provided (±)-2,3-dihydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate. To a solution of the tosylate in dimethylsulfoxide (50 mL) was added sodium azide (0.558 g, 8.59 mmol) and the reaction mixture was allowed to stir at 70° C. for 12 h, cooled to room temperature, diluted with water (200 mL) and extracted with diethyl ether (2×100 mL). The combined organic extracts were washed with water (4×75 mL), saturated aqueous sodium chloride (75 mL), dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:9) provided 1.38 g (71%) of (±)-2-(azidomethyl)-2,3-dihydronaphtho[1,2-b]furan as a colorless oil. Rf=0.46 (silica, ethyl acetate:hexanes 1:9); Anal. calcd. for C13H11N3O.0.1H2O: C, 68.77; H, 4.97; N, 18.51. Found: C, 68.4; H, 4.62; N, 18.12.
Sources & evidence
- ORD record
- ord-b4346d9bb1684cc28ec1b6bb56c53a12
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728155B2
Reaction notes
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