Water → 1alpha,3beta,25-Trihydroxy-cholest-5-en-23yne

HRID 1106226Notes

Reaction equation

HRID 1106226 reaction equation
O1CCCCC1[O:7][C@@H:8]1[C@@:39]2([CH3:40])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:41])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:34])[CH2:21][C:22]#[C:23][C:24]([O:27]C2CCCCO2)([CH3:26])[CH3:25])[CH2:11][C@@H:10]([O:42]C2CCCCO2)[CH2:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[OH:7][C@@H:8]1[C@@:39]2([CH3:40])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:41])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:34])[CH2:21][C:22]#[C:23][C:24]([OH:27])([CH3:25])[CH3:26])[CH2:11][C@@H:10]([OH:42])[CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 128511561alpha,3beta,25-tris[(tetrahydro-2H-pyran-2-yl)oxy]-cholest-5-en-23-yne

Product 1

HCID 133249571alpha,3beta,25-Trihydroxy-cholest-5-en-23yneYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.0 g (1.5 mmol) of 1α,3β,25-tris[(tetrahydro-2H-pyran-2-yl)oxyl]-cholest-5-en-23-yne in 14 ml of methanol was treated with 50 mg of p-toluenesulphonic acid monohydrate, and the mixture was left at room temperature for 1 hour. 16 ml of water was added dropwise while stirring. The separated material was filtered off under suction and dried. After chromatography on 60 g of silica gel with hexane/ether (1:1) and ethyl acetate, there was obtained 0.49 g (79%) of crystalline 1α,3β,25-trihydroxy-cholest-5-en-23yne of melting point 204°-206° C. Recrystallization of a sample from acetone gave crystals of melting point 205°-206° C.; [α]D25 =-12.6° (c=0.5 in methanol).

Workup

  1. filtrationThe separated material was filtered off under suction
  2. customdried

Sources & evidence

ORD record
ord-2de82bc179d043a992d1684bca4d14ca
Source dataset
uspto-grants-1982_01
Patent number
US04312812

Reaction notes

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