3,4-dihydro-2H-pyran → HCID 15907968, compound

HRID 2224041Notes

Reaction equation

HRID 2224041 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C(S(O)(=O)=O)=CC=CC=1.N1C=CC=CC=1.[O:24]=[C:25]1[CH2:42][C@@:40]2([CH3:41])[C@@H:36]([CH2:37][CH2:38][C@@H:39]2[OH:43])[C:35]2[CH2:34][CH2:33][C:32]3[CH:31]=[C:30]([O:44][CH3:45])[CH:29]=[CH:28][C:27]=3[C:26]1=2.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:45][O:44][C:30]1[CH:29]=[CH:28][C:27]2[C:26]3[C:25](=[O:24])[CH2:42][C@@:40]4([CH3:41])[C@@H:36]([CH2:37][CH2:38][C@@H:39]4[O:43][CH:6]4[CH2:5][CH2:4][CH2:3][CH2:2][O:1]4)[C:35]=3[CH2:34][CH2:33][C:32]=2[CH:31]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 15907984(17β)-17-Hydroxy-3-methoxyestra-1,3,5(10),8-tetraen-11-oneHCID 22058245HCID 22058245, compound

Product 1

HCID 15907968HCID 15907968, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

47 ml of dihydropyran and 0.96 g of pyridine toluenesufonate were added at room temperature to 15.29 g of 11-keto-3-methoxy-estra-1,3,5(10),8-tetraen-17β-ol (1) in 35 ml of dichloromethane, and it was stirred for 2 hours. Then, the reaction solution was shaken several times with saturated sodium bicarbonate solution, washed with water and dried with magnesium sulfate. The solvent was evaporated in a vacuum, and the residue was purified on silica gel (solvent mixture: cyclohexane/ethyl acetate=8/2). 16.8 g (83%) of light yellowish, viscous oil was thus obtained.

Workup

  1. washwashed with water
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was evaporated in a vacuum
  4. customthe residue was purified on silica gel (solvent mixture: cyclohexane/ethyl acetate=8/2)
  5. custom16.8 g (83%) of light yellowish, viscous oil was thus obtained

Sources & evidence

ORD record
ord-aab2de9c9916448bac54a21ec7eae880
Source dataset
uspto-grants-2008_05
Patent number
US07378404B2

Reaction notes

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