Water → HCID 67855518, compound

HRID 1587150Notes

Reaction equation

HRID 1587150 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[OH:29][CH2:30][C:31]([CH3:36])([CH3:35])[C:32](O)=[O:33].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[OH:33][CH2:32][C:31]([CH3:36])([CH3:35])[C:30]([O:19][C@H:18]1[CH2:20][CH2:21][C@@:22]2([CH3:23])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:17]1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 5997CholesterolHCID 6101p-Toluenesulfonic acidHCID 785483-Hydroxy-2,2-dimethylpropionic acid

Product 1

HCID 67855518HCID 67855518, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.6 g of cholesterol and 3.6 g of hydroxypivalic acid in 80 ml of toluene is treated with 1 g of p-toluenesulphonic acid and boiled for 4 hours. The reaction mixture is treated with water and extracted with ether. The organic phase is dried and concentrated and the residue is purified over silica gel with petroleum ether/ether (4:1). There are obtained 1.9 g of cholest-5-en-3β-yl 3-hydroxy-2,2-dimethyl-propionate, m.p. 174°-176° C.

Workup

  1. extractionextracted with ether
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customthe residue is purified over silica gel with petroleum ether/ether (4:1)

Sources & evidence

ORD record
ord-e01f1a5156bf4ad1ab01acd564e87db0
Source dataset
uspto-grants-1993_06
Patent number
US05215972

Reaction notes

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