HCID 67924073, compound → HCID 67924103, compound

HRID 1493663Notes

Reaction equation

HRID 1493663 reaction equation
[C:1]([CH2:6][C@:7]12[C:31]3[CH2:30][CH2:29][C@@H:28]4[C@:23]([CH3:33])([CH2:24][CH2:25][C@H:26]([OH:32])[CH2:27]4)[C:22]=3[CH2:21][CH2:20][C@:19]1([CH3:34])[C@@H:10]([C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9][CH2:8]2)([O:3]CC)=[O:2]>COCCOCCOC.[OH-].[Li+]>[C:1]([CH2:6][C@:7]12[C:31]3[CH2:30][CH2:29][C@@H:28]4[C@:23]([CH3:33])([CH2:24][CH2:25][C@H:26]([OH:32])[CH2:27]4)[C:22]=3[CH2:21][CH2:20][C@:19]1([CH3:34])[C@@H:10]([C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9][CH2:8]2)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 67924073HCID 67924073, compound

Product 1

HCID 67924103HCID 67924103, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8150DiglymeSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 14α-carbethoxymethyl-5α-cholest-8-en-3β-ol (100 mg) in diglyme (3 mL) and 1N lithium hydroxide (3 mL) was heated at 130° C. for 2 hours under argon. The cooled reaction was partitioned between methylene chloride and iced dilute HCl, and the dried and concentrated organic layer provided 65 mg of 14α-carboxymethyl-5α-cholest-8-en-3β-ol; mp 191°-193° C.

Workup

  1. customThe cooled reaction
  2. customwas partitioned between methylene chloride and iced dilute HCl
  3. customthe dried

Sources & evidence

ORD record
ord-65ea5db19d79496e9e3118fa638929f5
Source dataset
uspto-grants-1991_06
Patent number
US05023250

Reaction notes

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