Ammonium Chloride → HCID 86696722, compound

HRID 1774220Notes

Reaction equation

HRID 1774220 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[CH2:11][C:12](=[O:14])[CH3:13])=[CH:6][C:5]=1[F:16].[Cl-].[NH4+]>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[CH2:11][CH:12]([OH:14])[CH3:13])=[CH:6][C:5]=1[F:16]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86696721HCID 86696721, compound

Product 1

HCID 86696722HCID 86696722, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (112 mg, 2.95 mmol) was added in three portions to a solution of 4-(4-chloro-3-fluorophenyl)-4-hydroxybutan-2-one (160 mg, 0.73 mmol) in methanol (5 mL). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then treated with saturated ammonium chloride. After removal of methanol, the aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried and concentrated to give 1-(4-chloro-3-fluorophenyl)butane-1,3-diol (130 mg, 81% yield) as a solid. 1H NMR (500 MHz, CDCl3) δ 7.36 (m, 1H), 7.17 (m, 1H), 7.04 (m, 1H), 5.07 (m, 1H), 3.48 (br s, 1H), 2.13 (m, 1H), 1.56 (m, 1H), 1.30 (d, J=6.0 Hz, 3H).

Workup

  1. customAfter removal of methanol
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×25 mL)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-473e10c32d1f42f6ae5ec1c25ed776c9
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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