Triethylamine → HCID 54144580, compound

HRID 639141Notes

Reaction equation

HRID 639141 reaction equation
[N:1]1([CH2:7][CH:8]([OH:10])[CH3:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:18]=[C:19]1[O:23][C:21](=[O:22])[CH2:20]1>C1(C)C=CC=CC=1>[O:23]=[C:19]([CH3:18])[CH2:20][C:21]([O:10][CH:8]([CH3:9])[CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 979574-Morpholineethanol, .alpha.-methyl-

Product 1

HCID 54144580HCID 54144580, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5.0 g (34.4 mmol) 1-(4-Morpholinyl)-2-propanol and 35 mg (0.34 mmol) triethylamine are dissolved in 40 ml toluene. At 90° C., 3.76 g (44.77 mmol) diketene are added dropwise. The reaction mixture is stirred at 100° C. for one hour. After cooling down to room temperature, the mixture is poured into ice-water. The phases are separated and the water phase is extracted two times with toluene. 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 down to room temperature
  2. customThe phases are separated
  3. extractionthe water phase is extracted two times with toluene
  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-4e2c04db6d0e4ff1a5c40190eb2cbc47
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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