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

HRID 1524638ノート

反応式

HRID 1524638 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 min, (S)-trityl glycidyl ether (50.0 g) was added at the same temperature, and the mixture was stirred at RT for 30 min. Water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous MgSO4. 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). 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.09-3.13 (m, 1H), 3.20-3.23 (m, 1H), 4.26-4.29 (m, 1H), 5.14-5.32 (m, 2H), 5.76-5.84 (m, 1H), 7.23-7.45 (m, 15H).

後処理

  1. stirringthe mixture was stirred at RT for 30 min
  2. extractionfollowed by extraction with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  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-f7ecd8de211f4c9392882321ae70bc08
出典データセット
uspto-grants-2015_07
特許番号
US09079914B2

反応ノート

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