Borane → 4-(Hexadecyloxy)-3-(phenylmethoxy)-1-butanol
Reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:20]=[CH2:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].B.[O:31]1CCCC1>>[CH2:1]([O:17][CH2:18][CH:19]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:21][OH:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]Participants
Procedure
To a solution of 11.5 g of [[[1-[(hexadecyloxy)-methyl]-2-propenyl]oxy]methyl]benzene in 50 ml of tetrahydrofuran was added dropwise, at 0° C.,57.12 ml of 1 M borane in tetrahydrofuran. After stirring at room temperature for 3 hours the excess borane was destroyed by the addition of water. The mixture was cooled in an ice bath, 100 ml of 3N sodium hydroxide was added followed by 100 ml of 30% hydrogen peroxide and after 10 minutes the mixture was stirred for 1/2 hour at room temperature and then diluted with ether. The ether layer was separated, washed with brine, then saturated sodium bisulfite, dried over magnesium sulfate and the solvent removed. The residue was purified by HPLC [hexane: ethyl acetate (9:1)] giving 7.8 g of the desired compound as an oil.
Workup
- customwas destroyed by the addition of water
- temperatureThe mixture was cooled in an ice bath
- addition100 ml of 3N sodium hydroxide was added
- additiondiluted with ether
- customThe ether layer was separated
- washwashed with brine
- dry with materialsaturated sodium bisulfite, dried over magnesium sulfate
- customthe solvent removed
- customThe residue was purified by HPLC [hexane: ethyl acetate (9:1)]
Sources & evidence
- ORD record
- ord-faf215870bc84afd89541f411fd89a89
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04699990
Reaction notes
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