Diethyl Ether → 1alpha, 3beta-Bis(tetrahydropyran-2-yloxy)pregna-5,7-diene-20-carbaldehyde

HRID 1196396Notes

Reaction equation

HRID 1196396 reaction equation
[OH:1][C@@H:2]1[C@@:22]2([CH3:23])[C:6](=[CH:7][CH:8]=[C:9]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:24])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[CH:14]([CH:16]=[O:17])[CH3:15])[CH2:5][C@@H:4]([OH:25])[CH2:3]1.[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.[C:32]1(C)C=[CH:36][C:35](S(O)(=O)=O)=[CH:34][CH:33]=1.CC[O:45]CC>C(Cl)Cl>[O:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH:31]1[O:1][C@@H:2]1[C@@:22]2([CH3:23])[C:6](=[CH:7][CH:8]=[C:9]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:24])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[CH:14]([CH:16]=[O:17])[CH3:15])[CH2:5][C@@H:4]([O:25][CH:36]2[CH2:35][CH2:34][CH2:33][CH2:32][O:45]2)[CH2:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 538927811alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehyde

Product 1

HCID 228438971alpha, 3beta-Bis(tetrahydropyran-2-yloxy)pregna-5,7-diene-20-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride was dissolved 0.50 g of 1α,3β-dihydroxypregna-5,7-diene-20-carbaldehyde, followed by addition of 1 ml of 3,4-dihydropyran and 0.05 g of p-toluenesulfonic acid. The mixture was stirred at room temperature for 2 hours. The reaction mixture thus obtained was diluted with ether, washed successively with aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution, and dried over sodium sulfate, followed by concentration under reduced pressure. Finally the concentrate was purified by column chromatography to give 0.48 g of 1α,3β-bis(tetrahydropyran-2-yloxy)pregna-5,7-diene-20-carbaldehyde showing the following physical properties.

Workup

  1. customThe reaction mixture thus obtained
  2. washwashed successively with aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. customFinally the concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-88b3b7f513c041319f64270234627ae5
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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