Diethyl cyclopropane-1,1-dicarboxylate → HCID 68956592、化合物

HRID 2378072ノート

反応式

HRID 2378072 の反応式
C([Li])CCC.[C:6]([Si:10]([CH3:29])([CH3:28])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[N:26][OH:27])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)([CH3:9])([CH3:8])[CH3:7].[C:30]1([C:38](OCC)=[O:39])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:32][CH2:31]1>C1COCC1>[CH2:36]([O:35][C:33]([C:30]1([C:38]2([OH:39])[O:27][N:26]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([O:11][Si:10]([C:6]([CH3:7])([CH3:9])[CH3:8])([CH3:29])[CH3:28])=[CH:13][CH:14]=3)[CH:19]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:32][CH2:31]1)=[O:34])[CH3:37]

参加物

5

反応物 3

HCID 73790Diethyl cyclopropane-1,1-dicarboxylateHCID 72579577HCID 72579577、化合物HCID 178418339Butyllithium

生成物 1

HCID 68956592HCID 68956592、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

n-Butyllithium (2.5 M in hexane, 983.8 mL) is added to a solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-phenyl-ethanone oxime, which may be produced as in Example 136 (400 g) in THF (4 L) at 0° C. and the reaction solution is stirred for one hour at this temperature. Diethyl 1,1-cyclopropanedicarboxylate (227 mL) is added to the reaction solution, stirred for one hour at 0° C. and then the reaction is quenched with saturated ammonium chloride, diluted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure. The crude product is purified by column chromatography with 5-10% ethyl acetate in hexane to give a light yellow solid, which is triturated with pentane and filtered to give 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-hydroxy-4-phenyl-4,5-dihydro-isoxazol-5-yl}-cyclopropanecarboxylic acid ethyl ester (230.8 g.)

後処理

  1. stirringstirred for one hour at 0° C.
  2. customthe reaction is quenched with saturated ammonium chloride
  3. additiondiluted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customThe crude product is purified by column chromatography with 5-10% ethyl acetate in hexane
  9. customto give a light yellow solid, which
  10. customis triturated with pentane
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-d550e11fe0204cedb1cd8de31ba8aa84
出典データセット
uspto-grants-2008_12
特許番号
US07470715B2

反応ノート

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