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p-Toluenesulfonic acid → 7alpha-(5-Acetoxypentyl)-3,17beta-bis-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene

HRID 1595969
Notes
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Reaction equation

HRID 1595969 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([OH:28])[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C@@H:15]([OH:29])[CH2:14][CH2:13]1)(=[O:3])[CH3:2].[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1.[C:36]1(C)C=[CH:40][C:39](S(O)(=O)=O)=[CH:38][CH:37]=1.C(=O)(O)[O-:48].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([O:28][CH:35]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C@H:12]1[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C@@H:15]([O:29][CH:40]2[CH2:39][CH2:38][CH2:37][CH2:36][O:48]2)[CH2:14][CH2:13]1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 70191893HCID 70191893, compound

Product 1

HCID 206838777alpha-(5-Acetoxypentyl)-3,17beta-bis-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

5.6 g of crude 7α-(5-acetoxypentyl)-estra-1,3,5(10)-triene-3,17β-diol is dissolved in 35 ml of anhydrous tetrahydrofuran and mixed with 3.5 ml of dihydropyran and 0.18 g of p-toluenesulfonic acid. The mixture is stirred at room temperature overnight, then diluted with ethyl acetate, and the mixture is shaken out in succession with saturated sodium bicarbonate solution and saturated common salt solution. The organic phase is dried with sodium sulfate and concentrated by evaporation in a vacuum, yield 8.31 g.

Workup

  1. dry with materialThe organic phase is dried with sodium sulfate
  2. concentrationconcentrated by evaporation in a vacuum, yield 8.31 g

Sources & evidence

ORD record
ord-2c7fd111ceec4178a1e198cbe9d41cfa
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06288051B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes