Water → 3-Buten-2-ol, 1-(triphenylmethoxy)-, (2S)-

HRID 1693188ノート

反応式

HRID 1693188 の反応式
[Li][CH2:2]CCC.[I-].C[S+](C)C.[CH2:11]([O:15][C:16](C1C=CC=CC=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:12]1[O:14][CH2:13]1.O.[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1COCC1>[C:16]([O:15][CH2:11][C@@H:12]([OH:14])[CH:13]=[CH2:2])([C:38]1[CH:37]=[CH:36][CH:41]=[CH:40][CH:39]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

7

反応物 5

HCID 962WaterHCID 8058HexaneHCID 75127Trimethylsulfonium iodideHCID 7168113(S)-Glycidyl Trityl EtherHCID 178418339Butyllithium

生成物 1

HCID 114844683-Buten-2-ol, 1-(triphenylmethoxy)-, (2S)-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

A solution of n-BuLi in hexane (2.6 M; 182 mL) was added dropwise to a solution of trimethylsulfonium iodide (96.8 g) in THF (800 mL) at −30° C. After stirring at −20° C. for 20 minutes, (S)-trityl glycidyl ether (50.0 g) was added at the same temperature, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (52.0 g).

後処理

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionfollowed by extraction with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-2bd5a171319946ffab37adcf7fa6bb23
出典データセット
uspto-grants-2012_04
特許番号
US08158620B2

反応ノート

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