Sodium borohydride → HCID 68526007, compound

HRID 1990077Notes

Reaction equation

HRID 1990077 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[S:9][C:10](SC)=[C:11]([C:20]#[N:21])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)=[O:7])[CH3:4]>CCO>[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([C:20]#[N:21])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 68524438HCID 68524438, compound

Product 1

HCID 68526007HCID 68526007, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add NaBH4 (0.26 mmol) to a solution of 3-(4-iodophenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester, prepared in example E-3, in 2 mL of EtOH at 0° C. Remove the ice-bath and stir at room temperature. After 30 min, add additional NaBH4 (0.26 mmol) and stir and additional 30 minutes. Remove the solvent in vacuo and extract the residue with 50 mL of 1/9 MeOH/CH2Cl2. Evaporate and chromatograph (hexane:ethyl acetate 3:1) over silica gel to provide the title compound: MS (ES+, m/e): 384 (M+1).

Workup

  1. customRemove the ice-bath
  2. stirringstir and additional 30 minutes
  3. customRemove the solvent in vacuo
  4. extractionextract the residue with 50 mL of 1/9 MeOH/CH2Cl2
  5. customEvaporate

Sources & evidence

ORD record
ord-7b776dd26e4d45fe800474fea3e11101
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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