Imidazole → (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-ol

HRID 1437596ノート

反応式

HRID 1437596 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[C:14](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:15][OH:16])/[CH2:12][OH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].N1C=CN=C1.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C1COCC1.ClCCl.[Cl-].[Na+].O>[Si:32]([O:16][CH2:15]/[C:14](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[C:11](/[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)\[CH2:12][OH:13])([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33]

参加物

7

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57434773(2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol

生成物 1

HCID 58787782(2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-ol収率 17.5%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 110 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol and 50 g of imidazole in 1 L of THF stirred at −78° C., a solution 51 g of TBSCl in 250 mL of dichloromethane was added dropwise. The resulting mixture was stirred at −78° C. for 30 min. Brine was then added and warmed to room temperature. The organic phase was separated and the aqueous phase was extracted with EtOAc. The organic phases were combined and dried over Na2SO4 and evaporated. The resulting crude material was purified by flash chromatography to afford 25.6 g of the title compound as a white solid. 1H NMR (acetone-d6, 500 MHz): a 7.69 (d, 2H), 7.37 (d, 2H), 7.18-7.04 (m, 5M), 4.77 (s, 2H), 4.65 (d, 2H), 3.96 (t, 1H, OH), 3.03 (s, 3H), 0.84 (s, 9H), 0.01 (s, 6H).

後処理

  1. temperaturewarmed to room temperature
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe resulting crude material was purified by flash chromatography

出典と根拠

ORDレコード
ord-e9024b6858804734804e714fdf90e9db
出典データセット
uspto-grants-2009_11
特許番号
US07622502B2

反応ノート

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