Sodium borohydride → HCID 68899975, compound

HRID 735358Notes

Reaction equation

HRID 735358 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([S:20]([C:23]2[C:24]([CH:28]=[O:29])=[CH:25][S:26][CH:27]=2)(=[O:22])=[O:21])[CH:14]=[CH:13]3)=[CH:6][CH:5]=1>CO.C(Cl)Cl>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([S:20]([C:23]2[C:24]([CH2:28][OH:29])=[CH:25][S:26][CH:27]=2)(=[O:22])=[O:21])[CH:14]=[CH:13]3)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86616738HCID 86616738, compound

Product 1

HCID 68899975HCID 68899975, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (21 mg, 0.53 mmol) was added to a solution of 4-{[6-(4-fluorophenyl)naphthalen-2-yl]sulfonyl}thiophene-3-carbaldehyde (42 mg, 0.11 mmol) in MeOH (5 mL) and CH2Cl2 (2 mL) and the mixture stirred at ambient temperature. After 40 minutes, the mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL) and the organic fraction washed with brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo to afford solid material which was washed with Et2O and further dried in vacuo to yield (4-{[6-(4-fluorophenyl)naphthalen-2-yl]sulfonyl}-3-thienyl)methanol as a white solid (40 mg). 1H NMR (400 MHz, d6-DMSO): δ 8.70 (1H, s), 8.59 (1H, d, J=3.4 Hz), 8.34 (2H, t, J=6.2 Hz), 8.19 (1H, d, J=8.8 Hz), 8.03 (1H, dd, J=1.7, 8.6 Hz), 7.93-7.85 (3H, m), 7.53 (1H, d, J=3.4 Hz), 7.38 (2H, t, J=8.9 Hz), 5.31 (1H, t, J=5.6 Hz), 4.53 (2H, d, J=5.7 Hz). m/z (ES+) 384 [(M-OH)+].

Workup

  1. customthe mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL)
  2. washthe organic fraction washed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford solid material which
  7. washwas washed with Et2O
  8. customfurther dried in vacuo

Sources & evidence

ORD record
ord-c700aa6c0eaa4a40b5e75bb4f219d96a
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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