Water → HCID 57286567, compound

HRID 1659838Notes

Reaction equation

HRID 1659838 reaction equation
[O:1]1[C@H:3]2[C:4](=[O:24])[CH:5]=[C:6]3[C@:21]([CH3:22])([C@@H:2]12)[C@@H:20]1[C@H:9]([C@H:10]2[C@:17]([CH3:23])([CH2:18][CH2:19]1)[C@@H:13]([C@H:14]([OH:16])[CH3:15])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3.O.[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOCC>[O:1]1[C@H:3]2[C:4](=[O:24])[CH:5]=[C:6]3[C@:21]([CH3:22])([C@@H:2]12)[C@@H:20]1[C@H:9]([C@H:10]2[C@:17]([CH3:23])([CH2:18][CH2:19]1)[C@@H:13]([C@H:14]([O:16][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][O:26]1)[CH3:15])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 86738157HCID 86738157, compound

Product 1

HCID 57286567HCID 57286567, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.67 g (8.1 mmol) of (20R)-1α,2α-epoxy-20-hydroxy-pregna-4,6-dien-3-one in 120 ml of benzene is concentrated to 60 ml in a water-jet vacuum at 40° C., cooled to room temperature and to the suspension are added 1.6 ml of 3,4-dihydro-2H-pyran as well as 16 mg of anhydrous p-toluenesulphonic acid. The mixture is stirred at room temperature for 2.5 hours. The resulting solution is diluted with ether, washed with saturated sodium hydrogen carbonate solution and then with saturated sodium chloride solution, dried over sodium sulphate and evaporated. There are obtained 3.3 g of crystalline (20R)-1α,2α-epoxy-20-[(tetrahydro-2H-pyran-2-yl)oxy]-pregna-4,6-dien-3-one. Recrystallisation from ether containing 0.1% triethylamine yields colourless prisms of melting point 139°-140° C.; [α]D25 =+233.6° (c=0.5 in chloroform), UV (ethanol): λmax 291 nm (ε=20940).

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution
  2. dry with materialwith saturated sodium chloride solution, dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-8f7c7a96d8d54d30b10e0e563bbd6abf
Source dataset
uspto-grants-1981_12
Patent number
US04305881

Reaction notes

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