Dichloromethane → 4-(2-Fluorophenyl)-3-hydroxy-2-methylbutyl tosylate

HRID 2084739ノート

反応式

HRID 2084739 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:15])(O)[CH:10]([CH3:13])[CH2:11][OH:12].C(N(CC)CC)C.ClCCl.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>O>[S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)([O:12][CH2:11][CH:10]([CH3:13])[CH:9]([OH:15])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:34])=[O:33]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 227346504-(2-Fluorophenyl)-3-hydroxy-2-methylbutane-1,3-diol

生成物 1

HCID 120705744-(2-Fluorophenyl)-3-hydroxy-2-methylbutyl tosylate収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Under a nitrogen atmosphere, a mixture of 13.5 g (68.1 mmol) of 4-(2-fluorophenyl)-3-hydroxy-2-methylbutane-1,3-diol, 14.2 ml (21.3 mmol) of triethylamine, and 70 ml of dichloromethane was cooled with an ice bath and 13.0 g (68.1 mmol) of p-toluenesufonyl chloride was added to the mixture. After stirring overnight at room temperature, 100 ml of water was added thereto, followed by extraction 3 times each with 200 ml of dichloromethane, and the combined organic layer was dried with anhydrous sodium sulfate. After drying, the solvent was distilled off and the residue was purified by silica gel column chromatography to obtain 21.1 g of the title compound as a colorless oil. (Yield: 88%)

後処理

  1. temperaturewas cooled with an ice bath
  2. extractionfollowed by extraction 3 times each with 200 ml of dichloromethane
  3. dry with materialthe combined organic layer was dried with anhydrous sodium sulfate
  4. customAfter drying
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4e56efa2cda5482fb900e092ba09a00d
出典データセット
uspto-grants-2004_04
特許番号
US06717016B2

反応ノート

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