Water → HCID 70616853, compound

HRID 371983Notes

Reaction equation

HRID 371983 reaction equation
[O:1]=[C:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH:12]([C:14]([OH:16])=[O:15])[CH3:13])=[CH:3]1.[OH-].[Na+].[CH3:28]I.O>CN(P(N(C)C)N(C)C)C>[O:1]=[C:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH:12]([C:14]([O:16][CH3:28])=[O:15])[CH3:13])=[CH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 2205065327-60-6

Product 1

HCID 70616853HCID 70616853, compound

Reagents, catalysts & solvents 1

HCID 15355Hexamethylphosphorous triamideSolvent

Procedure

To a solution of 20 g (0.06 m) of 3-oxopregn-4-ene-20-carboxylic acid in 100 ml of hexamethyl phosphorus triamide is added 5.0 g (0.12 m) of sodium hydroxide as a 25% solution. The solution is stirred for 30 minutes after which 34 g (0.24 m) of methyliodide is added and stirring is continued for an additional 30 minutes. The reaction mixture is poured into 500 ml of water, and the product is collected and recrystallized from acetone to yield methyl 3-oxopregn-4-ene-20-carboxylate, M.P. 175°-177° C.

Workup

  1. additionis added
  2. customthe product is collected
  3. customrecrystallized from acetone

Sources & evidence

ORD record
ord-39b53bcbd69d4fd4a5085bf247aab855
Source dataset
uspto-grants-1978_05
Patent number
US04088760

Reaction notes

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