Ethyl bromoacetate → HCID 86740882, compound

HRID 745294Notes

Reaction equation

HRID 745294 reaction equation
[CH:1](=[C:8]1[C:12]2[O:13][C:14]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:15]=3[C:16](=[O:17])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH:1](=[C:8]1[C:12]2[O:13][C:14]3[CH:21]=[C:20]([O:22][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:19]=[CH:18][C:15]=3[C:16](=[O:17])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 54325690HCID 54325690, compound

Product 1

HCID 86740882HCID 86740882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzylidene-6-hydroxy-1,2,3,9-tetrahydro-cyclopenta[b][1]benzopyran-9-one (1.5 g) was reacted with ethyl 2-bromo-acetate (1.67 g) in dimethylformamide (60 ml), in the presence of anhydrous K2CO3 (1.38 g), under stirring at room temperature for 3 hours. The reaction mixture was diluted with ice water containing NaH2PO4 and the precipitated product was filtered and washed with water: crystallization from CH2Cl2 /methanol gave (3-benzylidene-1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1]benzopyran-6-yloxy)acetic acid, ethyl ester, m.p. 152°-154° C. (1.75 g), which was dissolved in dimethylformamide (22 ml) and treated with 2N NaOH (11.5 ml) at room temperature for 2 hours. The reaction mixture was acidified with 2N HCl and then diluted with ice water: the precipitated product was filtered and washed with water until neutral. Crystallization from CHCl3 /ethanol gave 1.4 g of (3-benzylidene-1,2,3,9-tetrahydro-9-oxo-cyclopenta[b][1 ]benzopyran-6-yloxy)-acetic acid, m.p. 277°-279° C.

Workup

  1. filtrationthe precipitated product was filtered
  2. washwashed with water
  3. customcrystallization from CH2Cl2 /methanol

Sources & evidence

ORD record
ord-756fb09d2e89441d84f9397399970641
Source dataset
uspto-grants-1986_07
Patent number
US04598090

Reaction notes

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