Benzene → HCID 12851169, compound

HRID 1105849Notes

Reaction equation

HRID 1105849 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]([CH3:28])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:27])[CH2:17][C@@H:18]2[OH:26])=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=[O:36])=CC=1.[O:40]1[CH:45]=[CH:44][CH2:43][CH2:42][CH2:41]1.[CH:46]1C=[CH:50][CH:49]=[CH:48][CH:47]=1>>[C:1]([O:4][CH2:5][C@@H:6]([CH3:28])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([O:27][CH:50]4[CH2:49][CH2:48][CH2:47][CH2:46][O:36]4)[CH2:17][C@@H:18]2[O:26][CH:45]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 12851167HCID 12851167, compound

Product 1

HCID 12851169HCID 12851169, compound

Procedure

To a solution of 2.7 g of (20S)-21-acetyloxy-20-methylpregn-5-ene-1α,3β-diol in 120 ml of benzene containing 30 mg of anhydrous p-toluenesulfonic acid was added 4.2 ml of 3,4-dihydro-2H-pyran. The reaction mixture was left at 20° for 2 hr. and then poured onto an ice-cold 5% sodium bicarbonate solution. The product was extracted with ether. The ether extract was washed with saturated sodium chloride solution, dried (Na2SO4) and evaporated under reduced pressure. After drying at 0.05 mm, 4.3 g of (20S)-21-acetoxy-1α,3β-bis[(tetrahydro-2H-pyran-2-yl)oxy]-20-methylpregn-5-ene was obtained which, after recrystallization from methanol--ether, had mp 155°-161°.

Workup

  1. extractionThe product was extracted with ether
  2. extractionThe ether extract
  3. washwas washed with saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customAfter drying at 0.05 mm

Sources & evidence

ORD record
ord-db5028213c1d4a35b1f3733c1bb8048d
Source dataset
uspto-grants-1982_01
Patent number
US04310467

Reaction notes

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