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

HRID 1921885ノート

反応式

HRID 1921885 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-27c563ef1bd54ad49ea1865950bb5fe8
出典データセット
uspto-grants-2012_05
特許番号
US08173704B2

反応ノート

読み込み中…