Water → 1 Alpha,25-dihydroxycholesterol

HRID 1106228Notes

Reaction equation

HRID 1106228 reaction equation
C(OC([O:6][C@@H:7]1[C@@:37]2([CH3:38])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:32])[CH2:20][CH2:21][CH2:22][C:23]([O:26]C(OCC)C)([CH3:25])[CH3:24])[CH2:10][C@@H:9]([O:40]C(OCC)C)[CH2:8]1)C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[OH:6][C@@H:7]1[C@@:37]2([CH3:38])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:32])[CH2:20][CH2:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[CH2:10][C@@H:9]([OH:40])[CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 543562811alpha,3beta,25-Tris(1-ethoxyethoxy)-cholest-5-ene

Product 1

HCID 1911241 Alpha,25-dihydroxycholesterolYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 36.2 g of 1α,3β,25-tris(1-ethoxyethoxy)-cholest-5-ene in 0.75 liters of methanol was treated with 5.6 g (29 mmol) of p-toluenesulphonic acid monohydrate, and the mixture was stirred at room temperature for 45 minutes. 1.8 liters of water was dropped into the solution. The suspension was suction filtered, and the residue was washed neutral with water and dried. There was obtained 21.3 g of 1α,3β,25-trihydroxycholest-5-ene which melted at 172°-175° C. after recrystallization from acetone.

Workup

  1. filtrationsuction filtered
  2. washthe residue was washed neutral with water
  3. customdried

Sources & evidence

ORD record
ord-426b3ef3a3424568b24af51b7b67ab06
Source dataset
uspto-grants-1982_01
Patent number
US04312812

Reaction notes

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