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

HRID 2268456
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HRID 2268456 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-35899d0b04194576bd07d2dbee129f8f
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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