p-Toluenesulfonic acid → (13S)-Ethyl-3-methoxygona-1,3,5(10),16-tetraen-17-ol Acetate

HRID 1650115Notes

Reaction equation

HRID 1650115 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:8]([C@H:9]4[C@@:13]([CH2:16][CH2:17]3)([CH2:14][CH3:15])[C:12](=[O:22])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([CH2:37][C:38]([O-])=[O:39])(C)=C>C(OCC)(=O)C>[C:38]([O:22][C:12]1[C@:13]2([CH2:16][CH2:17][C@H:18]3[C@@H:8]([CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:21]=[CH:20][C:19]=43)[C@@H:9]2[CH2:10][CH:11]=1)[CH2:14][CH3:15])(=[O:39])[CH3:37]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11087833EthylmetrienoneHCID 18355900Isopropenylacetate

Product 1

HCID 14257187(13S)-Ethyl-3-methoxygona-1,3,5(10),16-tetraen-17-ol Acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

30 g of 3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one [J. Org. Chem. 40 (1975) 681] is stirred for 22 hours at 120° C. in 200 ml of isopropenylacetate with 1.5 g of p-toluenesulfonic acid. It is then diluted with ethyl acetate, washed with sodium carbonate and a common salt (NaCl) solution, dried over sodium sulfate and concentrated. After chromatography, 27.6 g of 17-acetoxy-3-methoxy-18-methyl-1,3,5(10),16-estratetraene with a melting point of 105°-106° C. is obtained.

Workup

  1. washwashed with sodium carbonate
  2. dry with materiala common salt (NaCl) solution, dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4869d991748e4b459b42c88cccb69ecc
Source dataset
uspto-grants-1990_05
Patent number
US04923640

Reaction notes

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