Dimethylformamide → HCID 67369495, compound

HRID 2166863Notes

Reaction equation

HRID 2166863 reaction equation
O[C@@H:2]1[C@H:8]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH2:6][CH3:7])[C:4](=[O:21])[CH2:3]1)[C@@H:17]1[C:12](=[CH:13][CH2:14][CH2:15][CH2:16]1)[CH2:11][CH2:10]3.CS(Cl)(=O)=O.CN(C)C=O.C([O-])(=O)C.[Na+]>N1C=CC=CC=1>[CH3:7][CH2:6][C@:5]12[CH2:20][CH2:19][C@H:18]3[C@@H:9]([CH2:10][CH2:11][C:12]4[C@@H:17]3[CH2:16][CH2:15][CH2:14][CH:13]=4)[C@@H:8]1[CH:2]=[CH:3][C:4]2=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 31297Methanesulfonyl chlorideHCID 517045Sodium AcetateHCID 12801524HCID 12801524, compound

Product 1

HCID 67369495HCID 67369495, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In an ice bath, 7.8 g of 15α-hydroxy-18-methyl-4-estren-17-one in 50 ml of pyridine is combined with 10 ml of methanesulfonic acid chloride. After 1 hour, 50 ml of dimethylformamide (DMF) is added thereto, along with 23 g of anhydrous sodium acetate. The mixture is stirred for another 20 hours at room temperature. The mixture is introduced into ice/water. The thus-precipitated product is vacuum-filtered, washed with water, dissolved in ethyl acetate, and dried. Crystallization from ethyl acetate yields 5.1 g of 18-methyl-4,15-estradien-17-one, mp 125.2° C.

Workup

  1. filtrationThe thus-precipitated product is vacuum-filtered
  2. washwashed with water
  3. dissolutiondissolved in ethyl acetate
  4. customdried
  5. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-82f9264bb0e74aa383cd36657aa44139
Source dataset
uspto-grants-1983_06
Patent number
US04390530

Reaction notes

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