Dichloromethane → 2-fluoro-4-[(2E)-1-hydroxy-3-(1-trityl-1H-imidazol-5-yl)prop-2-enyl]benzonitrile

HRID 844265Notes

Reaction equation

HRID 844265 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10](=[O:37])/[CH:11]=[CH:12]/[C:13]2[N:17]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[N:15][CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(Cl)Cl.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[C:8]([CH:10]([OH:37])/[CH:11]=[CH:12]/[C:13]2[N:17]([C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:16]=[N:15][CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 230012962-fluoro-4-[(2E)-3-(1-trityl-1H-imidazol-5-yl)prop-2-enoyl]benzonitrile

Product 1

HCID 230013012-fluoro-4-[(2E)-1-hydroxy-3-(1-trityl-1H-imidazol-5-yl)prop-2-enyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product from Step E (8.89 g, 18.4 mmol) in methanol (200 mL)/methylene chloride (50 mL) at 0° C. was added sodium borohydride (695 mg, 18.4 mmol). After stirring for 1 hour, the reaction was quenched by the addition of sat. aq. NH4Cl until H2 evolution ceased. The solvents were removed in vacuo and the residue was partitioned between methylene chloride (200 mL) and water (200 mL). The layers were separated and the aqueous layer was washed with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide the title compound as a yellow oil which was sufficiently pure for use in the next step.

Workup

  1. customthe reaction was quenched by the addition of sat. aq. NH4Cl until H2 evolution
  2. customThe solvents were removed in vacuo
  3. customthe residue was partitioned between methylene chloride (200 mL) and water (200 mL)
  4. customThe layers were separated
  5. washthe aqueous layer was washed with methylene chloride (3×50 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41bae38ef3564ff5ace761eff8261fd2
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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