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

HRID 1921874

반응식

HRID 1921874 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-74494ef89d704db8a97c6cb4d099dcd0
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173704B2

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