Ethyl chloroformate → HCID 22823420, compound

HRID 2166682Notes

Reaction equation

HRID 2166682 reaction equation
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].[OH:7][C@@H:8]1[C@@:33]2([CH3:34])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:28])[CH2:21][CH2:22][C@@H:23]([OH:27])[CH:24]([CH3:26])[CH3:25])[CH2:11][C@@H:10]([OH:36])[CH2:9]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:3]([O:2][C:1]([O:7][C@@H:8]1[C@@:33]2([CH3:34])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:28])[CH2:21][CH2:22][C@@H:23]([O:27][C:1]([O:2][CH2:3][CH3:4])=[O:5])[CH:24]([CH3:26])[CH3:25])[CH2:11][C@@H:10]([O:36][C:1]([O:2][CH2:3][CH3:4])=[O:5])[CH2:9]1)=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 11026173HCID 11026173, compound

Product 1

HCID 22823420HCID 22823420, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A ethyl chlorocarbonate (24.75 ml) was added dropwise to a solution of 1α,3β,24(R)-trihydroxycholest-5-ene (3.63 g), 4-dimethylaminopyridine (6.25 g) and methylenechloride (40 ml) with stirring at 0° C. After stirring for 27 hours at 60° C., the reaction mixture was poured into ice water and extracted with methylenechloride. The extracts were washed with 2 N hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to give 4.98 g of residual product. The residue was recrystallized from methanol (10 ml) to afford 3.64 g of 1α,3β,24(R)-triethoxycarbonyoxycholest-5-ene as crystals.

Workup

  1. stirringAfter stirring for 27 hours at 60° C.
  2. extractionextracted with methylenechloride
  3. washThe extracts were washed with 2 N hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-67394c018d8c48f1ab000e666b6441f4
Source dataset
uspto-grants-1983_06
Patent number
US04388243

Reaction notes

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