Triethylamine → HCID 21110113, compound

HRID 639139Notes

Reaction equation

HRID 639139 reaction equation
[OH:1][C@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[CH2:15]=[C:16]1[O:20][C:18](=[O:19])[CH2:17]1>C1(C)C=CC=CC=1>[O:20]=[C:16]([CH3:15])[CH2:17][C:18]([O:1][C@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 637514(+)-Methyl lactate

Product 1

HCID 21110113HCID 21110113, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl(2R)-2-hydroxypropanoate (5.0 g, 48 mmol) and triethylamine (49 mg, 0.48 mmol) are dissolved in toluene (40 ml). At 90° C., diketene (5.2 g, 62.4 mmol) is added dropwise. The reaction mixture is stirred at 100° C. for one hour. After cooling to room temperature, the mixture is poured into ice-water. The phases are separated and the aqueous phase is extracted with toluene two times. The combined organic phases are dried over sodium sulfate, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethyl acetate mixtures as eluent.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with toluene two times
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customthe residue is purified by column chromatography on silica with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-65fd9d046b59447399fdaf8279fdbe60
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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