Imidazole → (E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

HRID 707673

反応式

HRID 707673 の反応式
[CH2:1]([OH:6])/[CH:2]=[CH:3]/[CH2:4][OH:5].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].O>CN(C=O)C>[Si:12]([O:5][CH2:4]/[CH:3]=[CH:2]/[CH2:1][OH:6])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 175854trans-2-Butene-1,4-diol

生成物 1

HCID 13841129(E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (2E)-2-butene-1,4-diol (8.22 mL, 0.10 mol) and imidazole (8.50 g, 0.125 mol) in DMF (50 mL) at 0° C., was added tert-butyldimethylsilyl chloride (7.50 g, 0.050 mol) in several portions over 10 minutes. The resulting mixture was warmed to room temperature and stirred (2 h), then poured into H2O (200 mL) and extracted with EtOAc (2×150 mL). The organic layer was washed (brine), dried (Na2SO4) and purified by silica gel column chromatography (hexanes:EtOAc) to yield 5 as a colorless oil (9.0 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 5.60-5.50 (m, 2H), 4.18 (m, 2H), 4.09 (m, 2H), 2.76 (br, 1H), 0.83 (s, 9H), 0.01 (s, 6H). 13C NMR (100 MHz, CDCl3) δ 136.3, 135.4, 64.8, 63.8, 31.1, 23.6.

後処理

  1. extractionextracted with EtOAc (2×150 mL)
  2. washThe organic layer was washed (brine)
  3. dry with materialdried (Na2SO4)
  4. custompurified by silica gel column chromatography (hexanes:EtOAc)

出典と根拠

ORDレコード
ord-4e446db5c6ca4c47a2c5d3010fa598b3
出典データセット
uspto-grants-2015_11
特許番号
US09175038B2

関連ノート

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