Methanol → HCID 62391057, compound
Reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12])[CH3:2].[BH4-].[Na+].CO.O>O1CCCC1>[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH:7]2[OH:12])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-Ethylindan-1-one (160 mg, 0.998 mmol) synthesized in (44A) was dissolved in tetrahydrofuran (5 mL), and the resulting solution was cooled to 0° C. Thereafter, sodium borohydride (57 mg, 1.50 mmol) was added thereto, and methanol (2 mL) was added dropwise thereto, and then, the resulting mixture was stirred at room temperature for 8 hours. Water was added to the reaction solution, and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound was obtained as a yellow oily substance (162 mg, yield: 100%).
Workup
- extractionthe organic matter was extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
- filtrationfiltered
- distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
- customwas obtained
- customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 70:30 (v/v)), whereby the objective title compound
- customwas obtained as a yellow oily substance (162 mg, yield: 100%)
Sources & evidence
- ORD record
- ord-3218ab7d50fa488086e8dbef772c07a6
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222281B2
Reaction notes
Loading…