Benzyl Chloride → HCID 69410835, compound

HRID 1764967Notes

Reaction equation

HRID 1764967 reaction equation
[OH:1][C@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@@H:4]([CH2:5][CH2:6][C:7]3[C:8]4[C@:19]([CH3:27])([CH2:20][CH2:21][C:22]=32)[C@@H:11]([C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH:9]=4)[C:3]1([CH3:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:36](Cl)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C>[CH2:36]([O:16][C:15](=[O:17])[CH2:14][CH2:13][C@H:12]([C@@H:11]1[C@:19]2([CH3:27])[C:8]([C:7]3[CH2:6][CH2:5][C@@H:4]4[C@:23]([C:22]=3[CH2:21][CH2:20]2)([CH3:26])[CH2:24][CH2:25][C@H:2]([OH:1])[C:3]4([CH3:28])[CH3:29])=[CH:9][CH2:10]1)[CH3:18])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 69410833HCID 69410833, compound

Product 1

HCID 69410835HCID 69410835, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3β-Hydroxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid (100 mg) is suspended in 5 ml of dry DMF. 811 mg of cesium carbonate and 0.29 ml of benzyl chloride is added and the mixture is stirred at 50° C. overnight. After aqueous work-up, column chromatography and crystallisation from acetone/water 55 mg of the title compound is obtained. Melting point: 118-119° C.

Workup

  1. customAfter aqueous work-up, column chromatography and crystallisation from acetone/water 55 mg of the title compound
  2. customis obtained

Sources & evidence

ORD record
ord-114533126f524954b22e0372a11c321d
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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