HCID 70403914, compound → HCID 70403452, compound

HRID 845250Notes

Reaction equation

HRID 845250 reaction equation
C([O:4][C@H:5]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=O)C>CO.N.C(OCC)C.CCCCCC>[OH:4][C@H:5]([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

5

Reactant 1

HCID 70403914HCID 70403914, compound

Product 1

HCID 70403452HCID 70403452, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 21584099Diethylether hexaneSolvent

Procedure

8.0 g of tert.butyl 2(R)-acetoxy-4-(4-nitrophenyl)butanoate were dissolved in 200 ml of methanol saturated with ammonia at 0° C. and the mixture was stirred for 16 hours. Evaporation of the mixture in vacuo gave 7 g of an almost colorless oil which was dissolved in an equal volume of diethyl ether/n-hexane (1:1) and eluted through a silica gel column with the same solvent mixture to give 6 g of tert.butyl 2(R)-hydroxy-4-(4-nitrophenyl)butanoate as a colorless crystalline solid having a melting point of 41°-42° C.

Workup

  1. customEvaporation of the mixture in vacuo
  2. customgave 7 g of an almost colorless oil which
  3. washeluted through a silica gel column with the same solvent mixture

Sources & evidence

ORD record
ord-ee81bc30d34d4c05967c8a43229e6c59
Source dataset
uspto-grants-1988_07
Patent number
US04757069

Reaction notes

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