Ethanol → HCID 86751728, compound

HRID 1939870Notes

Reaction equation

HRID 1939870 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[CH2:14][CH:13]([C:17]([F:20])([F:19])[F:18])[CH2:12][C:11]2=[O:21])=[CH:6][C:5]=1[CH:22]=[C:23]([Cl:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].O.[CH2:31]([OH:33])[CH3:32]>>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:21])[CH2:12][CH:13]([C:17]([F:19])([F:20])[F:18])[CH2:14][C:15]([O:33][CH2:31][CH3:32])=[O:16])=[CH:6][C:5]=1[CH:22]=[C:23]([Cl:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86751729HCID 86751729, compound

Product 1

HCID 86751728HCID 86751728, compound

Procedure

0.13 g (34 mmol) of sodium borohydride was added in portions at room temperature to a solution of 4.2 g (10 mmol) of N-[4-chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3-trifluoromethylglutarimide in 100 ml of ethanol. After stirring for 3 hours the reaction mixture was added to 100 ml of water, after which the aqueous phase was extracted twice with dichloromethane. The combined org. phases were dried over sodium sulfate and concentrated. Finally, the residue was purified by triturating with petroleum ether. Yield: 2 g (42%); m.p.: 115°-117° C.

Workup

  1. extractionafter which the aqueous phase was extracted twice with dichloromethane
  2. dry with materialphases were dried over sodium sulfate
  3. concentrationconcentrated
  4. customFinally, the residue was purified
  5. customby triturating with petroleum ether

Sources & evidence

ORD record
ord-e254e08c8a884ec9a6d81fd404179558
Source dataset
uspto-grants-1997_12
Patent number
US05698494

Reaction notes

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