Water → HCID 15086126, compound

HRID 1885560Notes

Reaction equation

HRID 1885560 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]1[CH2:30][C:29]2[CH:28]=[C:27]([OH:31])[CH:26]=[CH:25][C:24]=2[C@@H:23]2[C@@H:14]1[C@H:15]1[C@@:19]([CH2:21][CH2:22]2)([CH3:20])[C:18]2(OCC[O:32]2)[CH:17]=[CH:16]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]1[CH2:30][C:29]2[CH:28]=[C:27]([OH:31])[CH:26]=[CH:25][C:24]=2[C@@H:23]2[C@@H:14]1[C@H:15]1[C@@:19]([CH2:21][CH2:22]2)([CH3:20])[C:18](=[O:32])[CH:17]=[CH:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 22845805HCID 22845805, compound

Product 1

HCID 15086126HCID 15086126, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.6 g of 7α-(11-hydroxyundecyl)-17,17-ethylenedioxy-1,3,5(10),15-estratetraen-3-ol is stirred in 57 ml of acetone and 6.6 ml of water at 25° with 164 mg of p-toluenesulfonic acid for 2.5 hours. Then the mixture is concentrated to one-third, precipitated with ice/aqueous sodium chloride solution, filtered off, taken up in dichloromethane, washed neutral, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 2.3 g of crude 7α-(11-hydroxyundecyl)-1,3,5(10),15-estratetraen-3-ol-17-one, [α]D =-14.0°, as an oil.

Workup

  1. concentrationThen the mixture is concentrated to one-third
  2. customprecipitated with ice/aqueous sodium chloride solution
  3. filtrationfiltered off
  4. washwashed neutral
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-57bbe5ed99a74bf6bf0c2d916c4a8e5a
Source dataset
uspto-grants-1992_09
Patent number
US05145847

Reaction notes

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