Sodium borohydride → Methyl 4-(2-benzyloxyphenyl)butyrate

HRID 1533257Notes

Reaction equation

HRID 1533257 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22012346Methyl 4-(2-benzyloxyphenyl)crotonate

Product 1

HCID 22012370Methyl 4-(2-benzyloxyphenyl)butyrateYield 79.3%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a mixture of methyl 4-(2-benzyloxyphenyl)crotonate (14.4 g) and nickel chloride hexahydrate (1.19 g) in methanol (200 ml) was added portionwise sodium borohydride (3.78 g). During addition, the reaction temperature was kept at 20° C. by ice cooling. After the addition was completed, the mixture was stirred at ambient temperature for 1 hour and filtered. The filtrate was concentrated under reduced pressure. To the residue, water (100 ml) was added and the solution was extracted with diethyl ether. The organic layer was washed with brine, dried and evaporated in vacuo and the residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)] to give methyl 4-(2-benzyloxyphenyl)butyrate (11.5 g).

Workup

  1. additionDuring addition
  2. customwas kept at 20° C. by ice cooling
  3. additionAfter the addition
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionTo the residue, water (100 ml) was added
  7. extractionthe solution was extracted with diethyl ether
  8. washThe organic layer was washed with brine
  9. customdried
  10. customevaporated in vacuo
  11. customthe residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)]

Sources & evidence

ORD record
ord-fb415ea29c71487c85107d68d0aa252e
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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