2-Chloroethanol → HCID 15428861, compound

HRID 1003734Notes

Reaction equation

HRID 1003734 reaction equation
[H-].[Na+].[CH2:3]([Cl:6])[CH2:4][OH:5].[CH2:7]([O:9][C:10](=[O:16])[CH2:11][C:12]([CH2:14]Br)=[O:13])[CH3:8].Cl>O1CCCC1>[CH2:7]([O:9][C:10](=[O:16])[CH2:11][C:12]([CH2:14][O:5][CH2:4][CH2:3][Cl:6])=[O:13])[CH3:8]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 575284Ethyl 4-bromo-3-oxobutanoate

Product 1

HCID 15428861HCID 15428861, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.38 g (0.25 mole) of 57.8% sodium hydride are added to 110 ml of tetrahydrofurane. The mixture is cooled to a temperature between -10° C. and -20° C. whereupon at this temperature 10.08 g (0.125 mole) of ethylene chlorohydrine (III) are added under nitrogen dropwise. The mixture is stirred for 20 minutes, whereupon at the same temperature a solution of 26.18 g (0.125 mole) of ethyl-4-bromoacetoacetate (II) and 35 ml of tetrahydrofurane is added. The reaction mixture is stirred for 20 minutes, allowed to warm to room temperature, kept at this temperature for 6 hours, poured into 270 ml of 1 N hydrochloric acid under cooling and extracted with dichloro methane. The organic layer is dried and evaporated. The residual oil is made free of paraffine by treatment with a 1:1 mixture of acetonitrile and benzene. The product is distilled off in vacuo. Thus 17.47 g of the desired compound are obtained, yield 67%, bp.: 110° C./2 Hgmm.

Workup

  1. additionare added under nitrogen dropwise
  2. additionis added
  3. waitkept at this temperature for 6 hours
  4. temperatureunder cooling
  5. extractionextracted with dichloro methane
  6. customThe organic layer is dried
  7. customevaporated
  8. additionThe residual oil is made free of paraffine by treatment with a 1:1 mixture of acetonitrile and benzene
  9. distillationThe product is distilled off in vacuo

Sources & evidence

ORD record
ord-1fec2fb33cd34da093a1184a49fd0350
Source dataset
uspto-grants-2000_04
Patent number
US06046337

Reaction notes

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