Benzene → HCID 13044103, compound

HRID 1701489Notes

Reaction equation

HRID 1701489 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:18]1[C@H:20]2[C:21](=[O:42])[CH:22]=[C:23]3[C@:39]([CH3:40])([C@@H:19]12)[C@@H:38]1[C@H:26]([C@H:27]2[C@:35]([CH3:41])([CH2:36][CH2:37]1)[C@@H:30]([C@H:31]([CH3:34])[CH2:32][OH:33])[CH2:29][CH2:28]2)[CH:25]=[CH:24]3.C1C=CC=CC=1>CCOCC>[O:18]1[C@H:20]2[C:21](=[O:42])[CH:22]=[C:23]3[C@:39]([CH3:40])([C@@H:19]12)[C@@H:38]1[C@H:26]([C@H:27]2[C@:35]([CH3:41])([CH2:36][CH2:37]1)[C@@H:30]([C@H:31]([CH3:34])[CH2:32][O:33][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH2:29][CH2:28]2)[CH:25]=[CH:24]3

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 13044100HCID 13044100, compound

Product 1

HCID 13044103HCID 13044103, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.8 ml. of 3,4-dihydro-2H-pyran and 20 mg of anhydrous p-toluenesulphonic acid were added to a solution of 2.45 g of (20S)-1α,2α-epoxy-21-hydroxy-20-methyl-pregna-4,6-dien-3-one in 125 ml. of absolute benzene. After standing at room temperature for 1 hour, the solution was diluted with ether, washed with saturated sodium bicarbonate solution and water, dried over sodium sulphate and concentrated in a water-jet vacuum. The residue was chromatographed on 30 g of silica gel using hexane/ether (4:1) for the elution, there being obtained 2.0 g (65%) of (20S)-1α,2α-epoxy-20-methyl-21-tetrahydropyranyloxy-pregna-4,6-dien-3-one. After recrystallisation from hexane, the product melted at 101°-102° C. and was shown by thin-layer chromatography, mixed melting point and IR spectrum to be identical with the compound prepared as described in Example 7.

Workup

  1. washwashed with saturated sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in a water-jet vacuum
  4. customThe residue was chromatographed on 30 g of silica gel
  5. washfor the elution, there

Sources & evidence

ORD record
ord-1f788b31417349549661d19064269396
Source dataset
uspto-grants-1980_03
Patent number
US04193921

Reaction notes

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