Methanol → HCID 69335833, compound

HRID 478996Notes

Reaction equation

HRID 478996 reaction equation
COC(=O)[C@@H](C1C=CC=[CH:8][C:7]1([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[O:12][C:13]([O:16][CH3:17])([CH3:15])[CH3:14])O.[BH4-].[Na+].C[OH:29]>>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C@@H:7]([O:12][C:13]([O:16][CH3:17])([CH3:14])[CH3:15])[CH2:8][OH:29])=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 131724205HCID 131724205, compound

Product 1

HCID 69335833HCID 69335833, compound

Procedure

Into methanol (20 ml) were added (R)-2-(4-chlorophenyl)-2-(1-methoxy-1-methylethyloxy)mandelic acid methyl ester obtained in 2) above (6.0 g) and further, under ice-cooling, sodium borohydride (4.35 g). The resulting mixture was stirred at the same temperature, neutralized and the reaction mixture was concentrated. Ethyl acetate and water were added to the resulting residue and the organic layer was collected by layer separation. The organic layer was washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off to obtain a colorless oily compound mentioned above (5.2 g, 96.7%).

Workup

  1. customobtained in 2) above (6.0 g)
  2. temperaturefurther, under ice-cooling
  3. concentrationthe reaction mixture was concentrated
  4. additionEthyl acetate and water were added to the resulting residue
  5. customthe organic layer was collected by layer separation
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered off
  9. distillationthe solvent was distilled off
  10. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-b0b60a1fca0c4400be845ceef5ca0418
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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