Hydrochloric Acid → 1,3-Difluoro-5-hydroxymethyl-2-triisopropylsilanyloxybenzene

HRID 1921874

Reaction equation

HRID 1921874 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:21])[C:9]=1[O:10][Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:5]=[O:6].O.[BH4-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([F:21])[C:9]=1[O:10][Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 579719203,5-Difluoro-4-triisopropylsilanyloxybenzaldehyde

Product 1

HCID 579718961,3-Difluoro-5-hydroxymethyl-2-triisopropylsilanyloxybenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

35.0 g (111 mmol) of 3,5-difluoro-4-triisopropylsilanyloxybenzaldehyde are introduced into 150 ml of water and 40 ml of methanol, cooled to 0° C. and, after addition of 8.42 g (222 mmol) of sodium borohydride in portions, stirred at RT overnight. The mixture is cautiously acidified with 1 N hydrochloric acid and extracted with ethyl acetate, and the combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent is distilled out in vacuo. Chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 4:1) results in 29.5 g (93.2 mmol, 84% of theory) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent is distilled out in vacuo

Sources & evidence

ORD record
ord-74494ef89d704db8a97c6cb4d099dcd0
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Linked notes

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