Triethylamine → HCID 13217113, compound

HRID 1381045Notes

Reaction equation

HRID 1381045 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:19][CH:20]([CH3:24])[C:21](Br)=[O:22]>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:21](=[O:22])[CH:20]([Br:19])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121412-(Benzyloxy) ethanolHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 13217113HCID 13217113, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-5 °C

Procedure

15.2 g of 2-benzyloxyethanol and 10.6 g of triethylamine were dissolved in 150 ml of toluene, and the solution was cooled to -5° C. A solution of 21.6 g of 2-bromopropionylbromide in 30 ml of toluene was added dropwise thereto at -5° to 0° C. with stirring. The reaction mixture was further maintained at room temperature for two hours. The mixtue was then washed successively with 1% strength by weight sodium hydroxide solution and water, and the toluene solution was then dried and filtered. The toluene was distilled off under reduced pressure, and the end product of 2-benzyloxyethyl-2-bromopropionate was obtained in a yield of 26.7 g (nD20.5 1.5182)

Workup

  1. temperatureThe reaction mixture was further maintained at room temperature for two hours
  2. washThe mixtue was then washed successively with 1% strength by weight sodium hydroxide solution and water
  3. dry with materialthe toluene solution was then dried
  4. filtrationfiltered
  5. distillationThe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d4eedf43f6fa4508b7ecc44307e2cdae
Source dataset
uspto-grants-1986_04
Patent number
US04584396

Reaction notes

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