Water → HCID 20559491, compound

HRID 1659562Notes

Reaction equation

HRID 1659562 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:19])[CH2:17][CH3:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([O:19][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH3:18])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 20559480HCID 20559480, compound

Product 1

HCID 20559491HCID 20559491, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1 g., 50% w/w suspension in mineral oil) was added gradually to a stirred solution of 1-[4-(4-chlorophenyl)phenyl]propanol (4.9 g.) in dry dimethylformamide (20 ml.), keeping the temperature below 40° C. After 2 hours stirring ethyl bromoacetate (2.3 ml.) was then added, keeping the temperature below 30° C. After stirring for 16 hours at room temperature, the mixture was poured into water (150 ml.), and the subsequent mixture was extracted with ether. The combined extracts were washed with water, dried (MgSO4) and evaporated to give ethyl 2-{1-[4-(4-chlorophenyl)-phenyl]propoxy}acetate as an oil (5 g.).

Workup

  1. customthe temperature below 40° C
  2. additionwas then added
  3. customthe temperature below 30° C
  4. extractionthe subsequent mixture was extracted with ether
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-be33663df3514a3588fb3f5a6b9c6f01
Source dataset
uspto-grants-1981_12
Patent number
US04304788

Reaction notes

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