Hydrogen Peroxide → 3-(4-Phenylbutoxy)propan-1-ol
Reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH-:24].[Na+].OO>C1COCC1>[C:9]1([CH2:8][CH2:7][CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH2:3][OH:24])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of Intermediate 11 (0.40 g, 2.10 mmol) in THF (5 mL) was cooled to 0° C. A 0.5 M solution of BBN (5 mL, 2.52 mmol) in THF was added, and the resulting mixture was stirred 1 hour at 0° C. and 2 hours at room temperature. A solution of 2M NaOH (1 mL) and hydrogen peroxide (1 mL, 35%) was successively added and the mixture stirred 1 hour at room temperature. The solution was then concentrated and the residue dissolved in ether (25 mL), washed with water (2×15 mL) and brine (5 mL), dried (Na2SO4) and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1) afforded the title compound (0.24 g, 55%) as oil.
Workup
- stirringthe mixture stirred 1 hour at room temperature
- concentrationThe solution was then concentrated
- dissolutionthe residue dissolved in ether (25 mL)
- washwashed with water (2×15 mL) and brine (5 mL)
- dry with materialdried (Na2SO4)
- customthe solvent removed under reduced pressure
- customPurification of the residue by column chromatography on silica gel (hexane/AcOEt, 6:1)
Sources & evidence
- ORD record
- ord-24c19d371f384d62adc87bb3c575c45a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242177B2
Reaction notes
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