Water → methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate

HRID 465625Notes

Reaction equation

HRID 465625 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH:21]=[O:22])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH2:21][OH:22])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10357812methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate

Product 1

HCID 10380582methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the crude methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate (2.44 g crude) in ethanol (22 ml) is added sodium borohydride (0.307 g, 8.1 mmol). The reaction is stirred for 15 minutes and then poured into water. The pH of the mixture is adjusted to 8.0 using saturated sodium bicarbonate solution. The mixture is extracted with methylene chloride (3×30 ml) and the combined organic extracts are dried, filtered and evaporated to give an oil. This is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent to yield methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)-octanoate (oil), [alpha]D25 -1.22° (c 1.02 in methanol).

Workup

  1. extractionThe mixture is extracted with methylene chloride (3×30 ml)
  2. customthe combined organic extracts are dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil
  6. customThis is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-c34269d5450540fbb4a489cb196d0ddb
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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