Toluene → 7beta-Methyl-3-tetrahydropyranyloxy-estra-1,3,5(10)-trien-17-one

HRID 369058Notes

Reaction equation

HRID 369058 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[C@@H:6]([CH3:21])[CH2:5][C:4]=2[CH:3]=1.C1(C)C=CC(S(O)(=O)=[O:29])=CC=1.[C:33]1(C)C=[CH:37][CH:36]=[CH:35][CH:34]=1>O1C=CCCC1.C(OCC)(=O)C>[CH3:21][C@H:6]1[CH2:5][C:4]2[CH:3]=[C:2]([O:1][CH:37]3[CH2:36][CH2:35][CH2:34][CH2:33][O:29]3)[CH:19]=[CH:18][C:17]=2[C@@H:16]2[C@@H:7]1[C@H:8]1[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 56624864HCID 56624864, compound

Product 1

HCID 183970847beta-Methyl-3-tetrahydropyranyloxy-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 2

HCID 80803,4-dihydro-2H-pyranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1.2 g of 3-hydroxy-7β-methyl-estra-1,3,5(10)-trien-17-one in 12 ml of toluene and 1.2 ml of dihydropyran is stirred with 5.6 mg of para-toluenesulfonic acid for 2 hours at room temperature. Then, it is diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/acetone. 1.22 g of 7β-methyl-3-tetrahydropyranyloxy-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. washwashed with sodium bicarbonate solution as well as with saturated sodium chloride solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with hexane/acetone

Sources & evidence

ORD record
ord-cc80cb39a167476bad58b2699ae9cb84
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

Loading…