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

HRID 2268456
Notes
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Reaction equation

HRID 2268456 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

2
HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-35899d0b04194576bd07d2dbee129f8f
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes