Water → HCID 44375456, compound

HRID 479313Notes

Reaction equation

HRID 479313 reaction equation
Cl[CH2:2][C@@H:3]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C:13]([C:14]3[CH2:15][CH2:16][C@@H:17]4[C@:22]([C:24]=3[CH2:25][CH2:26]2)([CH3:23])[CH2:21][CH2:20][C@H:19]([OH:29])[C:18]4([CH3:31])[CH3:30])=[CH:12][CH2:11]1)[CH3:9])[CH3:4].[I-:32].[Na+].O>CC(C)=O>[I:32][CH2:2][C@@H:3]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C:13]([C:14]3[CH2:15][CH2:16][C@@H:17]4[C@:22]([C:24]=3[CH2:25][CH2:26]2)([CH3:23])[CH2:21][CH2:20][C@H:19]([OH:29])[C:18]4([CH3:31])[CH3:30])=[CH:12][CH2:11]1)[CH3:9])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 44375477HCID 44375477, compound

Product 1

HCID 44375456HCID 44375456, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of (25R)-26-chloro-4,4-dimethyl-5α-cholesta-8,14-dien-3β-ol (50 mg, 0.1 mmol) and sodium iodide (0.8 g) in acetone (3 mL) were heated at 55° C. in a sealed reaction vessel for 3 days. Addition of water, extraction with diethyl ether and concentration under reduced pressure gave a residue which was crystallised 3 times from hexane to give the title compound (37 mg).

Workup

  1. concentrationwith diethyl ether and concentration under reduced pressure
  2. customgave a residue which
  3. customwas crystallised 3 times from hexane

Sources & evidence

ORD record
ord-f340476261cd4e1abd9a1a646e4b5678
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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