Diethyl Carbonate → HCID 54236099, compound

HRID 1586637Notes

Reaction equation

HRID 1586637 reaction equation
[C:1]([O:4][C:5]1[CH:26]=[CH:25][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+].[C:33](=O)([O:37]CC)[O:34][CH2:35][CH3:36]>O>[CH2:35]([O:34][C:33]([CH2:2][C:1]([O:4][C:5]1[CH:26]=[CH:25][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:7][CH:6]=1)=[O:3])=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 19758718HCID 19758718, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54236099HCID 54236099, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The product from (b) (42 g, 0.12 mol) was added portionwise to a suspension of potassium t-butoxide (21.3 g, 0.19 mol) in diethyl carbonate (56.6 g, 0.48 mol) at 75° C. over 10 minutes. Heating was continued at 95° C. for 1 h. After cooling to 50° C., the suspension was poured into cold water (1 liter) and extracted with ethyl acetate (3×400 ml). The organic solution was dried and evaporated under reduced pressure to give the product (47 g, 93%) as a yellow waxy solid which was used in the next reaction without further purification.

Workup

  1. temperatureHeating
  2. extractionextracted with ethyl acetate (3×400 ml)
  3. customThe organic solution was dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f1dfbf44fc0f45c48c2bb42587ebcae6
Source dataset
uspto-grants-1993_06
Patent number
US05215878

Reaction notes

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