Ethyl Acetate → HCID 5317588, compound

HRID 1059033Notes

Reaction equation

HRID 1059033 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:23])[CH2:9][C:10]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([O:21][CH3:22])[CH:15]=1)=[O:11].[BH4-].[Na+].CCOC(C)=O>CCO>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][CH:10]([OH:11])[CH2:9][CH:8]([OH:23])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH:15][C:16]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 168114(8)-GingerolHCID 4311764Sodium borohydride

Product 1

HCID 5317588HCID 5317588, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of [8]-gingerol (0.1 g) in EtOH (15 mL) was added dropwise a solution of NaBH4 (0.02 g in 1 mL H2O). The mixture was stirred at room temperature for 3 hrs. After acidification, EtOAc was added and organic layer was washed with water twice. Evaporation of solvent left a white solid which was purified by gradient chromatography to afford the title compound as a colourless liquid in quantitative yield.

Workup

  1. washorganic layer was washed with water twice
  2. customEvaporation of solvent
  3. waitleft a white solid which
  4. customwas purified by gradient chromatography

Sources & evidence

ORD record
ord-763d659ed08b4fbb86f943100e1d3d23
Source dataset
uspto-grants-2003_02
Patent number
US06518315B1

Reaction notes

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