Succinic anhydride → HCID 70464371, compound

HRID 325599Notes

Reaction equation

HRID 325599 reaction equation
[O:1]=[C:2]1[CH:26]=[C:25]2[C@:20]([CH3:28])([CH2:21][CH2:22][C@H:23]([OH:27])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:29])([CH2:17][CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:6][CH2:5]1.[C:30]1(=[O:36])[O:35][C:33](=[O:34])[CH2:32][CH2:31]1>N1C=CC=CC=1>[C:30]([OH:35])(=[O:36])[CH2:31][CH2:32][C:33]([OH:1])=[O:34].[O:1]=[C:2]1[CH:26]=[C:25]2[C@:20]([CH3:28])([CH2:21][CH2:22][C@H:23]([OH:27])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:29])([CH2:17][CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 91474(3beta)-3-Hydroxycholest-5-en-7-one

Product 1

HCID 70464371HCID 70464371, compoundYield 166.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 5 g of 7-ketocholesterol was dissolved in 50 ml pyridine, 1.8 g of succinic anhydride was added thereto, the mixture was heated to react for 8 hours at 90° C. and allowed to stand at room temperature overnight. Then, the resulting liquid was poured into 500 ml ice-cold water. The crystals precipitated by acidification with hydrochloric acid were collected by filtration and then dissolved in ethanol, active carbon was added thereto for decoloration and filtered off, water was added to the filtrate, and the precipitated crystals were recovered by filtration. Upon recrystallization thereof from aqueous ethanol, 5.4 g of 7-ketocholesterol succinic acid half ester was obtained as flaky crystals, m.p. 187.5°-189.5° C.

Workup

  1. temperaturethe mixture was heated
  2. customto react for 8 hours at 90° C.
  3. customThe crystals precipitated by acidification with hydrochloric acid
  4. filtrationwere collected by filtration
  5. dissolutiondissolved in ethanol
  6. additionactive carbon was added
  7. filtrationfor decoloration and filtered off
  8. additionwater was added to the filtrate
  9. filtrationthe precipitated crystals were recovered by filtration
  10. customUpon recrystallization

Sources & evidence

ORD record
ord-9e01c45f3b6b4567bbdacf7b7c6969dc
Source dataset
uspto-grants-1984_04
Patent number
US04442037

Reaction notes

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