Sodium hydride → HCID 20559484, compound

HRID 1659558Notes

Reaction equation

HRID 1659558 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionateHCID 2769545HCID 2769545, compound

Product 1

HCID 20559484HCID 20559484, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.8 g., 80% w/w dispersion in mineral oil) was added to a stirred solution of 2-[4-(4-chlorophenyl)phenyl]-ethanol (5.0 g.) in dimethylformamide (20 ml.). The mixture was stirred at room temperature under nitrogen for 5 hours. Ethyl 2-bromopropionate (3 ml.) was then added and the mixture was stirred at room temperature. After 18 hours the mixture was partitioned between ethyl acetate (100 ml.) and 4-N-hydrochloric acid (100 ml.). The organic phase was separated, washed with water (30 ml.), and evaporated to give ethyl 2-{2-[4-(4-chlorophenyl)phenyl]ethoxy}propionate as an oil (7.0 g.).

Workup

  1. stirringthe mixture was stirred at room temperature
  2. customAfter 18 hours the mixture was partitioned between ethyl acetate (100 ml.) and 4-N-hydrochloric acid (100 ml.)
  3. customThe organic phase was separated
  4. washwashed with water (30 ml.)
  5. customevaporated

Sources & evidence

ORD record
ord-9f9a02ce5b944a91845b6541771abd66
Source dataset
uspto-grants-1981_12
Patent number
US04304788

Reaction notes

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