2-Chloroethanol → HCID 17825646, compound

HRID 1297037Notes

Reaction equation

HRID 1297037 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].[H-].[Na+].Br[CH2:8][C:9](=[O:29])[CH2:10][C:11]([O:13][CH2:14][CH2:15][CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:12].Cl>O1CCCC1>[Cl:1][CH2:2][CH2:3][O:4][CH2:8][C:9](=[O:29])[CH2:10][C:11]([O:13][CH2:14][CH2:15][CH:16]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:12]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 17825575HCID 17825575, compound

Product 1

HCID 17825646HCID 17825646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2.09 g (26 mmol) of 2-chloroethanol in 10 ml of tetrahydrofuran was added dropwise to a suspension of 1.84 g (46 mmol) of sodium hydride (60% oily) in 100 ml of tetrahydrofuran at −50° C., and they were stirred for 2 hours. A solution of 7.51 g (20 mmol) of 3,3-diphenylpropyl 4-bromoacetoacetate in 3 ml of tetrahydrofuran was added dropwise to the reaction mixture at −50° C. The temperature was elevated to room temperature, and they were stirred overnight. A small amount of hydrochloric acid was added to the reaction mixture. After the concentration followed by the fractionation with ethyl acetate and water, the extract was washed with 1 N sodium hydroxide and saturated aqueous sodium chloride solution and then dried over sodium sulfate to obtain the title compound.

Workup

  1. customwas elevated to room temperature
  2. stirringthey were stirred overnight
  3. concentrationAfter the concentration
  4. washthe extract was washed with 1 N sodium hydroxide and saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-0583deb3c778490fbce212aba9177ea0
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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