p-Toluenesulfonic acid → HCID 67576705, compound

HRID 1455909Notes

Reaction equation

HRID 1455909 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:26][C@@:24]3([CH3:25])[C@@H:20]([CH2:21][CH2:22][C:23]3=[O:27])[C@H:19]3[C@H:10]2[C@@H:11]2[C:16]([CH2:17][CH2:18]3)=[CH:15][C:14](=[O:28])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.[CH2:29](OC(OCC)OCC)[CH3:30].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)C>[CH2:29]([O:28][C:14]1[CH2:13][CH2:12][C@H:11]2[C:16](=[CH:17][CH2:18][C@@H:19]3[C@@H:10]2[C@@H:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:26][C@@:24]2([CH3:25])[C@H:20]3[CH2:21][CH2:22][C:23]2=[O:27])[CH:15]=1)[CH3:30]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 9821134HCID 9821134, compound

Product 1

HCID 67576705HCID 67576705, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

10 g of 11β-(4-methoxyphenyl)-4-oestrene-3,17-dione are placed in a mixture of 260 ml of absolute methylene chloride, 29 ml of ethanol and 26.4 ml of orthoformic acid triethyl ester and, at 0° C., 100 mg of p-toluenesulphonic acid (monohydrate) are added. The whole is then stirred for 3.5 hours at ice-bath temperature and then an excess of saturated sodium hydrogen carbonate solution is added to the reaction mixture. The aqueous phase is extracted repeatedly with methylene chloride and the combined organic phases are dried over sodium sulphate and concentrated in vacuo. The crude product is used directly in the subsequent reaction step. 10.8 g of crude 3-ethoxy-11β-(4-methoxyphenyl)-3,5-oestradien-17-one are isolated.

Workup

  1. extractionThe aqueous phase is extracted repeatedly with methylene chloride
  2. dry with materialthe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product is used directly in the subsequent reaction step

Sources & evidence

ORD record
ord-2e5094462a9142a698a9f77805f58a96
Source dataset
uspto-grants-1998_12
Patent number
US05843931

Reaction notes

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