Sodium borohydride → HCID 23372725, compound

HRID 1899085Notes

Reaction equation

HRID 1899085 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](Cl)=[O:14])=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][OH:14])=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23372722HCID 23372722, compound

Product 1

HCID 23372725HCID 23372725, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carbonyl chloride (1.2 g) and sodium borohydride (0.21 g) in dioxane (15 ml) was stirred at ambient temperature for 2 hours. The mixture was diluted with ethyl acetate, washed with water, dilute hydrochloric acid, an aqueous solution of sodium bicarbonate, successively, dried and concentrated. The residue (1.2 g) was recrystallized from ethanol to give pale brown crystals of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-methanol (0.55 g).

Workup

  1. washwashed with water, dilute hydrochloric acid
  2. dry with materialan aqueous solution of sodium bicarbonate, successively, dried
  3. concentrationconcentrated
  4. customThe residue (1.2 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-fdace3452ee749b68c3135741d90156c
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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