Carbon Dioxide → Cholesta-1,5,7-trien-3-on-25-ol

HRID 2397524Notes

Reaction equation

HRID 2397524 reaction equation
[CH3:1][C:2]([OH:29])([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH:19]=[CH:20]2)[CH:15]=[CH:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].CC(C)([O-])C.[K+].[K].C(=O)=O>O.C(O)CCC.CCOCC.CS(C)=O>[CH3:1][C:2]([OH:29])([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C:18](=[O:28])[CH:19]=[CH:20]2)=[CH:15][CH:14]=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3]

Participants

9

Reactant 4

HCID 280Carbon Dioxide2×HCID 5462222PotassiumHCID 2279738725-Hydroxycholesta-1,4,6-trien-3-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22797385Cholesta-1,5,7-trien-3-on-25-ol

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A reaction vessel was charged with 125 ml of dry dimethylsulfoxide and 2.5 g of cholesta-1,4,6-trien-3-on-25-ol was suspended in the dimethylsulfoxide. The suspension was heated, and 10 ml of dry ether was added to the resulting milky suspension to obtain a transparent solution. The reaction vessel was filled with dry argon gas. Powdery potassium t-butoxide prepared from 1.25 g potassium and 50 ml of butanol was added at one time to the solution under ice cooling and with violent agitation. The reaction mixture liquid was violently agitated for 12 minutes and was then poured into ice water saturated with carbon dioxide gas, which was prepared by adding dry ice to water. The mixture was then extracted with 600 ml of ether cooled to 0° to 5° C. The extract was promptly washed with cooled water saturated with a large quantity of carbon dioxide until the washing liquid became neutral, and the ether was then distilled off to obtain crude cholesta-1,5,7-trien-3-on-25-ol.

Workup

  1. temperatureThe suspension was heated
  2. customto obtain a transparent solution
  3. additionThe reaction vessel was filled with dry argon gas
  4. additionwas added at one time to the solution under ice cooling and with violent agitation
  5. customwas prepared
  6. extractionThe mixture was then extracted with 600 ml of ether
  7. temperaturecooled to 0° to 5° C
  8. washThe extract was promptly washed with cooled water saturated with a large quantity of carbon dioxide until the washing liquid
  9. distillationthe ether was then distilled off

Sources & evidence

ORD record
ord-88a9042828054b91b46d372a7215c06f
Source dataset
uspto-grants-1977_05
Patent number
US04022768

Reaction notes

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