Triethylamine → HCID 59609082, compound

HRID 1631858Notes

Reaction equation

HRID 1631858 reaction equation
[OH:1][C:2]([CH3:12])([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[Cl:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>O1CCCC1>[CH3:11][C:2]([O:1][C:23](=[O:24])[CH2:22][CH2:21][Cl:20])([CH3:12])[C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-one

Product 1

HCID 59609082HCID 59609082, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

9.9 g (60 mmol) 2-hydroxy-2-methyl-1-phenyl-1-propanone (DAROCUR™ 1173) was dissolved in 60 ml tetrahydrofuran. 6.1 g (60 mmol) triethyl amine was added and the reaction mixture was cooled to −10° C. 7.6 g (60 mmol) 3-chloro-propionyl chloride was added while the temperature was kept below −5° C. The reaction was allowed to continue for 30 minutes at 0° C. and for 72 hours at 40° C. The precipitated salts were removed by filtration and the solvent was evaporated under reduced pressure. 3-chloro-propionic acid 1,1-dimethyl-2-oxo-2-phenylethyl ester was purified by preparative column chromatography on a Prochrom LC80 column, using n.-hexane/ethyl acetate 80/20 as eluent at a flow rate of 150 ml/min and Kromasil 60A 10 micron as silica. 1 g of 3-chloro-propionic acid 1,1-dimethyl-2-oxo-2-phenylethyl ester was isolated.

Workup

  1. customwas kept below −5° C
  2. customThe precipitated salts were removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. custom3-chloro-propionic acid 1,1-dimethyl-2-oxo-2-phenylethyl ester was purified by preparative column chromatography on a Prochrom LC80 column

Sources & evidence

ORD record
ord-1fe742810ac54c1388fdfa4b359767e9
Source dataset
uspto-grants-2014_07
Patent number
US08791289B2

Reaction notes

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