2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehyde → (2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)methanol
Reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:15])[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([CH:13]=[O:14])[C:6]=2[O:5]1>C(O)C>[CH3:3][C:4]1([CH3:15])[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([CH2:13][OH:14])[C:6]=2[O:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (1.08 grams, 0.0285 mole) was added carefully in small portions to a stirred solution of 2,3-dihydro-2,2-dimethylbenzofuran-7-carboxaldehyde (10.0 grams, 0.057 mole) in ethanol (150 ml) at 5°-10° C. during a ten minute period. The reaction mixture was stirred for thirty minutes and was then quenched by the dropwise addition of water (25 ml) followed by 10% hydrochloric acid (25 ml). The reaction mixture was concentrated under reduced pressure leaving a residue. This residue was partitioned between diethyl ether (75 ml) and 10% hydrochloric acid (30 ml). The layers were separated, and the organic layer was washed with water (40 ml) and a saturated aqueous solution of sodium chloride (40 ml). The dried (sodium sulfate) organic solution was concentrated under reduced pressure, yielding 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethanol as a solid. The NMR spectrum was consistent with the proposed structure.