Dimethylformamide → Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylate

HRID 2268461Notes

Reaction equation

HRID 2268461 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:23][C:22]3[C:17](=[C:18]([O:30][CH3:31])[C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[C:21]=3[O:24][CH3:25])[CH2:16]2)=[CH:11][CH:10]=1.Br[CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>O>[CH2:44]([O:43][C:41]([CH2:40][CH2:39][CH2:38][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:16][C:17]3[C:22](=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[C:19]([O:28][CH3:29])[C:18]=3[O:30][CH3:31])[CH2:23]2)=[CH:13][CH:14]=1)=[O:42])[CH3:45]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 18348564Ethyl 2-(4-hydroxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate

Product 1

HCID 18348634Ethyl 2-[4-(4-ethoxycarbonyl-1-oxabutyl)phenyl]-4,5,6,7-tetramethoxy-2-indancarboxylateYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% oily, 9.8 mg, 0.244 mmols) was added to a DMF (2 ml) solution of ethyl 2-(4-hydroxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate (81.5 mg, 0.203 mmols), with cooling with ice. The reaction mixture was stirred at room temperature for 30 minutes, and ethyl 4-bromobutyrate (0.0600 ml, 0.406 mmols) was dropwise added thereto at room temperature, and stirring was continued for 3 hours. Water was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out, 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 (85.1 mg) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. stirringat room temperature, and stirring
  3. waitwas continued for 3 hours
  4. extractionwas then extracted with diethyl ether
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and then dried
  7. customThe solvent was evaporated out
  8. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-8415eae67b704e19b4924ea7c6972de4
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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