Ammonium Chloride → Methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzoate

HRID 1921885노트

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HRID 1921885 반응식
[C:1]([CH:4]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[C:20]([F:36])[CH:19]=1)[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(O)=[O:2].[Cl-].[NH4+]>C1COCC1>[F:36][C:20]1[CH:19]=[C:18]([CH:23]=[C:22]([F:24])[C:21]=1[O:25][Si:26]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:33]([CH3:34])[CH3:35])[CH2:17][CH:4]([CH2:1][OH:2])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1

참가 물질

4

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HCID 25517Ammonium ChlorideHCID 57971897Methyl 4-[3-carboxy-4-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)butyl]benzoate

생성물 1

HCID 57971911Methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

4.2 g (8.07 mmol) of methyl 4-[3-carboxy-4-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)butyl]-benzoate are dissolved in 200 ml of THF and cooled to −10° C. under argon. Then 16.13 ml (16.13 mmol) of a 1 M borane-THF complex solution are added dropwise, and the mixture is stirred at 0° C. until reaction is complete. The mixture is hydrolyzed with saturated ammonium chloride solution and extracted with diethyl ether, and the combined organic phases are concentrated. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1→10:1→4:1). 2.92 g (71% of theory) of the title compound are obtained.

후처리

  1. additionThen 16.13 ml (16.13 mmol) of a 1 M borane-THF complex solution are added dropwise
  2. extractionextracted with diethyl ether
  3. concentrationthe combined organic phases are concentrated
  4. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1→10:1→4:1)

출처 및 근거

ORD 기록
ord-27c563ef1bd54ad49ea1865950bb5fe8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173704B2

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