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Acetic Acid → Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-1-oxo-2-indancarboxylate

HRID 2268456
ノート
印刷プレビュー

反応式

HRID 2268456 の反応式
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:48](OCC)=[O:49])([CH2:32][C:33]2[C:38](Br)=[C:37]([O:40][CH3:41])[C:36]([O:42][CH3:43])=[C:35]([O:44][CH3:45])[C:34]=2[O:46][CH3:47])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>C(OCC)C.C1COCC1>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:32][C:33]3[C:38](=[C:37]([O:40][CH3:41])[C:36]([O:42][CH3:43])=[C:35]([O:44][CH3:45])[C:34]=3[O:46][CH3:47])[C:48]2=[O:49])=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8058HexaneHCID 18348651Ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionateHCID 178418339Butyllithium

生成物 1

HCID 18348626Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-1-oxo-2-indancarboxylate収率 47.2%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A hexane solution of n-butyl lithium (1.68 M, 11.3 ml, 19.0 mmols) was dropwise added to a THF (100 ml) solution of ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionate (10.0 g, 15.8 mmols), under a nitrogen stream at −90° C or lower. The reaction mixture was stirred for 30 minutes, and a THF (10 ml) solution of acetic acid (1.86 g, 31.6 mmols) was dropwise added thereto still at −90° C. or lower. The reaction mixture was allowed to warm to room temperature, and diluted with diethyl ether. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to obtain the entitled compound (3.78 g) as an oil.

後処理

  1. customstill at −90° C.
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution, water
  3. dry with materiala saturated aqueous sodium chloride solution, and then dried
  4. customThe solvent was evaporated out in vacuo
  5. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

出典と根拠

ORDレコード
ord-35899d0b04194576bd07d2dbee129f8f
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326369B1

反応ノート

読み込み中…

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