Triethylamine → HCID 59684880, compound

HRID 421793Notes

Reaction equation

HRID 421793 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:20])[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:28]=[C:29]1[O:33][C:31](=[O:32])[CH2:30]1>C1(C)C=CC=CC=1>[O:33]=[C:29]([CH3:28])[CH2:30][C:31]([O:20][CH:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 2476141,3-Bis(benzyloxy)propan-2-ol

Product 1

HCID 59684880HCID 59684880, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

1.00 g (3.67 mmol) 1,3-dibenzyloxy-2-propanol is dissolved in 10 ml toluene, 3.72 mg (0.04 mmol) triethylamine are added, and the mixture is stirred at 90° C. 401 mg (4.77 mmol) diketene are added, and stirring is continued for 1 h. The mixture is cooled to room temperature, diluted with ice-water and extracted with toluene. The organic layer is dried over magnesium sulfate and evaporated to dryness. The crude product is purified by column chromatography on silica gel (eluent: cyclohexane/ethylacetate 2:1).

Workup

  1. stirringstirring
  2. temperatureThe mixture is cooled to room temperature
  3. extractionextracted with toluene
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe crude product is purified by column chromatography on silica gel (eluent: cyclohexane/ethylacetate 2:1)

Sources & evidence

ORD record
ord-68044aab589e48d69dccc16e22ea9d70
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Reaction notes

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