Pyridine → HCID 22795299, compound

HRID 1974430Notes

Reaction equation

HRID 1974430 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14](=[CH:15][C@H:16]([OH:23])[CH2:17][CH2:18]1)[CH2:13][C@H:12]3[CH3:24])(=[O:3])[CH3:2].N1C=CC=CC=1.C[C:32]1[CH:33]=[CH:34][C:35](S(O)(=O)=O)=[CH:36][CH:37]=1.[O:42]1CCOC[CH2:43]1>>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14](=[CH:15][C@H:16]([O:23][C:32]2([O:42][CH3:43])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[CH2:17][CH2:18]1)[CH2:13][C@H:12]3[CH3:24])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 68131708HCID 68131708, compound

Product 1

HCID 22795299HCID 22795299, compound

Procedure

The compound 7α-methylestr-4-en-3α,17β-diol 17-acetate is dissolved in anhydrous dioxane and treated with pyridine, p-toluenesulfonate and cyclohexanone methyl enolether. Stirring is continued for a period of 3 hours. The solvent is removed in vacuo and the residue is crystallized from pentane resulting in the formation of the desired 7α-methyl-3α-(1'-methoxycyclohexyloxy)estr-4-en-17β-ol acetate.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is crystallized from pentane resulting in the formation of the desired 7α-methyl-3α-(1'-methoxycyclohexyloxy)estr-4-en-17β-ol acetate

Sources & evidence

ORD record
ord-f5723c13855d428baf94ab6161428070
Source dataset
uspto-grants-1976_12
Patent number
US04000273

Reaction notes

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