Reaction equation
C[O-].[Na+].[SH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[BH4-].[Na+].CS(O[CH2:19][CH:20]([O:41][CH3:42])[CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])(=O)=O>O.C1COCC1.CO>[OH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][S:4][CH2:19][CH:20]([O:41][CH3:42])[CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To 14 ml of a methanol solution of sodium methoxide (1M solution) are added 2.04 g of 6-mercaptohexanol and 0.24 g of sodium borohydride, to which a THF (20 ml) solution containing 2.18 g of 2-methoxy-3-octadecyloxypropyl methanesulfonate is added dropwise under nitrogen streams with stirring. The mixture is stirred at room temperature for 20 hours and then at 40° C. for 1 hour. After the addition of water, the mixture is extracted with ethyl acetate. The extracted layer is washed with water, dried and concentrated under reduced pressures to obtain an oily product. Purification of the oily product by silica gel column chromatography gives 2.31 g of the captioned compound.
Workup
- additionis added dropwise under nitrogen streams
- stirringThe mixture is stirred at room temperature for 20 hours
- extractionthe mixture is extracted with ethyl acetate
- washThe extracted layer is washed with water
- customdried
- concentrationconcentrated under reduced pressures
- customto obtain an oily product
- customPurification of the oily product by silica gel column chromatography
Sources & evidence
- ORD record
- ord-4c91898a85ad49d3857d98c9dbfe87a3
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04845219
Linked notes
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