Sodium borohydride → HCID 11596162, compound

HRID 1351676Notes

Reaction equation

HRID 1351676 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([S:19]([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH:24]=[O:25])(=[O:21])=[O:20])=[CH:15][CH:14]=1>CO.C(Cl)Cl>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1/[CH:11]=[CH:12]/[C:13]1[CH:14]=[CH:15][C:16]([S:19]([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH2:24][OH:25])(=[O:20])=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21099432HCID 21099432, compound

Product 1

HCID 11596162HCID 11596162, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (89 mg, 1.8 mmol) was added to a solution of 2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzaldehyde (Step 1; 233 mg, 0.61 mmol) in MeOH (7 mL) and CH2Cl2 (3 mL). After 2 h, the mixture was partitioned between CH2Cl2 (10 mL) and water (10 mL), the phases were separated and the aqueous portion extracted with further CH2Cl2 (10 mL). The combined organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant 40% EtOAc/isohexane) gave the title compound as a white solid (208 mg). δH (500, d6 DMSO): 8.08 (1H, d, J 7.7), 7.89–7.83 (5H, m), 7.77 (1H, d, J 7.6), 7.72 (1H, t, J 7.4), 7.55 (1H, t, J 7.5), 7.42–7.34 (2H, m), 7.33–7.27 (1H, m), 7.15 (1H, td, J 2.1, 8.4), 5.39 (1H, t, J 5.7), 4.69 (2H, d, J 5.7). m/z (ES+) 369 [(M−OH)+].

Workup

  1. customthe mixture was partitioned between CH2Cl2 (10 mL) and water (10 mL)
  2. customthe phases were separated
  3. extractionthe aqueous portion extracted with further CH2Cl2 (10 mL)
  4. dry with materialThe combined organics were then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (eluant 40% EtOAc/isohexane)

Sources & evidence

ORD record
ord-d0364039da214877bb78e914653b5ec9
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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