Trimethylsulfonium iodide → HCID 86747263, compound

HRID 1655649Notes

Reaction equation

HRID 1655649 reaction equation
[CH2:1]1[CH2:14][O:13][C:8]23[O:9][CH2:10][CH2:11][O:12][C:3]2([C@:4]2([CH2:29][CH2:28][C@H:27]4[C@@H:17]([CH2:18][CH2:19][C@@H:20]5[C@:25]4([CH3:26])[C:24](=[CH2:30])[CH2:23][CH2:22][CH2:21]5)[C@@H:6]2[C@H:7]3[CH:15]=[O:16])[CH3:5])[O:2]1.[I-].[CH3:32][S+](C)C.CC([O-])(C)C.[K+]>CN(C)C=O.ClCCl>[CH2:11]1[CH2:10][O:9][C:8]23[O:13][CH2:14][CH2:1][O:2][C:3]2([C@:4]2([CH2:29][CH2:28][C@H:27]4[C@@H:17]([CH2:18][CH2:19][C@@H:20]5[C@:25]4([CH3:26])[C:24](=[CH2:30])[CH2:23][CH2:22][CH2:21]5)[C@@H:6]2[C@H:7]3[CH:15]2[CH2:32][O:16]2)[CH3:5])[O:12]1

Participants

6

Reactant 3

HCID 75127Trimethylsulfonium iodideHCID 23665647Potassium tert-butoxideHCID 86747264HCID 86747264, compound

Product 1

HCID 86747263HCID 86747263, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3.8 g of 3,3;17,17-bis(ethylenedioxy)-1-methylene-5α-androstane-15α-carbaldehyde in 46 ml of dimethylformamide is stirred under argon with 3.0 g of trimethylsulfonium iodide and 2.3 g of potassium tert-butylate at room temperature. After 30 minutes the reaction mixture is added to ice/water. The precipitated product is suctioned off, dissolved in dichloromethane, washed neutral with water. 3.5 g of 3,3;17,17-bis(ethylenedioxy)-1-methylene-15α-(2-oxiranyl)5α-androstane is obtained as foam.

Workup

  1. washwashed neutral with water

Sources & evidence

ORD record
ord-5487ad814109440e879cba40750aaea1
Source dataset
uspto-grants-1993_10
Patent number
US05250712

Reaction notes

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