Triethylsilane → HCID 178444127、化合物

HRID 271330

反応式

HRID 271330 の反応式
C(C1CC(C)(C)CCC1(O[SiH3])[C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15](=[O:23])[NH:16][C:17]2=[O:22])(C)(C)C.C([SiH]([CH2:31][CH3:32])CC)C.[CH3:33][CH:34]([CH3:46])[CH2:35][CH:36]=[C:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH:38]=[O:39].[Bi](Br)(Br)Br>C(#N)C>[CH3:33][CH:34]([CH3:46])[CH2:35][CH:36]=[C:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:38][O:39][C@H:32]1[CH2:31][CH2:15][C@H:14]([N:16]2[C:15](=[O:23])[C:14]3[C:18](=[CH:19][CH:20]=[CH:21][CH:13]=3)[C:17]2=[O:22])[CH2:13][CH2:21]1

参加物

6

反応物 4

HCID 12052TriethylsilaneHCID 82232bismuth(III) bromideHCID 5760265-Methyl-2-phenylhex-2-enalHCID 1317271834-(Tert-butyl-dimethyl-silyloxy-cyclohexyl)-isoindole-1,3-dione

生成物 1

HCID 178444127HCID 178444127、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred mixture of 1 g of trans-2-(4-(tert-butyl-dimethyl-silyloxy-cyclohexyl)-isoindole-1,3-dione, 20 mL of anhydrous acetonitrile, 0.8 mL of triethylsilane and 0.6 g of 5-methyl-2-phenyl-2-hexenal (commercial, predominantly trans was added ) 0.08 g of bismuth tribromide. After stirring for 1.3 h, the reaction was quenched with 10 mL of saturated sodium bicarbonate and extracted with 3×25 mL portions of ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 1%-20% ethyl acetate in hexane gave first 0.30 g of saturated product, trans-2-[4-(5-methyl-2-phenyl-hexyloxy)-cyclohexyl]-isoindole-1,3-dione, then 0.50 g of product as a resin: 1H NMR (400 MHz, CDCl3) 7.8 (m, 2H), 7.7 (m, 2H), 7.3-7.1 (m, 5H), 5.8 (t, 1H), 4.25 (s, 2H), 4.15 (m, 2H), 3.4 (m, 1H), 2.3 (m, 2H), 2.1 (d, 2H), 1.9 (t, 2H), 1.75 (d, 2H), 1.65 (, 1H), 1.35 (m, 2H), 1.3 (t, 2H), 0.9 (d, 6H).

後処理

  1. customthe reaction was quenched with 10 mL of saturated sodium bicarbonate
  2. extractionextracted with 3×25 mL portions of ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-eb971e799883495db1832a8aa0a418e0
出典データセット
uspto-grants-2008_11
特許番号
US07452893B2

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