Sodium borohydride → HCID 67338337, compound

HRID 1675838

Reaction equation

HRID 1675838 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:17]#[N:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=1[F:19]>CCO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]#[N:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=1[F:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67338173Ethyl 3-(4-chloro-3-fluorophenyl)-2-cyanoacrylate

Product 1

HCID 67338337HCID 67338337, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution NaBH4 (15 mg, 0.39 mmol) in EtOH (4 mL) was cannulated into a mixture of the ethyl 3-(4-chloro-3-fluorophenyl)-2-cyanoacrylate (200 mg, 0.79 mmol) in EtOH (2 mL) at room temperature. After 5 minutes, the mixture was quenched with 0.1N HCl, concentrated in vacuo, diluted with H2O, extracted with DCM, dried over MgSO4, concentrated and subject to flash chromatography (SiO2 with DCM) to give ethyl 3-(4-chloro-3-fluorophenyl)-2-cyanopropanoate (0.20 g, 58%). LCMS (APCI+) [M+H]+ 254.3.

Workup

  1. customthe mixture was quenched with 0.1N HCl
  2. concentrationconcentrated in vacuo
  3. additiondiluted with H2O
  4. extractionextracted with DCM
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-246e67dbb011467fad6b6d373b4ffde8
Source dataset
uspto-grants-2011_08
Patent number
US08003651B2

Linked notes

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