Acetic Acid → HCID 73675547, compound

HRID 569280Notes

Reaction equation

HRID 569280 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:16][CH:17]=[C:18]([Cl:20])[CH3:19])([CH2:13][CH2:14][CH3:15])[C:8]2=[O:12])=[CH:4][C:3]=1[CH:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23].[H-].[Na+].Br[CH2:35][C:36]([O:38][CH3:39])=[O:37].C(O)(=O)C>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:39][O:38][C:36]([CH2:35][C:21]([C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([Cl:11])[C:2]=1[Cl:1])[C:8](=[O:12])[C:7]([CH2:16][CH:17]=[C:18]([Cl:20])[CH3:19])([CH2:13][CH2:14][CH3:15])[CH2:6]2)([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:37]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 54492079HCID 54492079, compound

Product 1

HCID 73675547HCID 73675547, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Diethyl 2-[6,7-dichloro-2-(3-chloro-2-butenyl)-2,3-dihydro-1-oxo-2-propyl-1H-inden-5-yl]malonate (10.7 g, 0.0218 mole) dissolved in toluene (45 ml) was added dropwise with stirring under N2 at 25° C. to a suspension of 56% sodium hydride/mineral (1.22 g, 0.0284 mole) in dimethylformamide (45 ml). Methyl bromoacetate (4.34 g, 0.0284 mole) was added in one portion 40 minutes after the previous addition and the mixture was heated at 65° for 41/2 hours. The mixture was then cooled, and after acetic acid (3 ml) was added, poured into ice water and extracted with diethyl ether. The organic extracts were washed with water, dried over MgSO4, concentrated under vacuum, and the residue was chromatographed on silica eluting with methlene chloride/hexane, 4/1 to obtain 10.9 g of the product as an oil.

Workup

  1. additionwas added dropwise
  2. additionafter the previous addition
  3. temperaturethe mixture was heated at 65° for 41/2 hours
  4. temperatureThe mixture was then cooled
  5. extractionextracted with diethyl ether
  6. washThe organic extracts were washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under vacuum
  9. customthe residue was chromatographed on silica eluting with methlene chloride/hexane, 4/1

Sources & evidence

ORD record
ord-f124e51671dc464a8588031f7cdc2354
Source dataset
uspto-grants-1988_03
Patent number
US04731472

Reaction notes

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