Butanethiol → HCID 53861741, compound

HRID 543019Notes

Reaction equation

HRID 543019 reaction equation
[S-:1][CH2:2][CH2:3][CH2:4][CH3:5].[Na+].C(S)CCC.[H-].[Na+].C([O:17][C@H:18]1[CH2:23][CH2:22][C@H:21]2[C@H:24]3[C@H:33]([CH2:34][CH2:35][C@:19]12[CH3:20])[C:32]1[CH:31]=[CH:30][C:29]([O:36]C(=O)C2C=CC=CC=2)=[CH:28][C:27]=1[CH2:26][C@H:25]3[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]OS(C)(=O)=O)(=O)C>O1CCCC1>[CH2:2]([S:1][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][C@@H:25]1[CH2:26][C:27]2[CH:28]=[C:29]([OH:36])[CH:30]=[CH:31][C:32]=2[C@@H:33]2[C@@H:24]1[C@H:21]1[C@@:19]([CH2:35][CH2:34]2)([CH3:20])[C@@H:18]([OH:17])[CH2:23][CH2:22]1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 8012ButanethiolHCID 24758Sodium hydrideHCID 35309931-Butanethiol, sodium saltHCID 56616798HCID 56616798, compound

Product 1

HCID 53861741HCID 53861741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium thiobutoxide [generated from butanethiol (0.045 g.) and a 60% dispersion of sodium hydride in mineral oil (0.02 g.)] in tetrahydrofuran (2 ml.) was added to a solution of 17β-acetoxy-3-benzoyloxy-7α-(11-methanesulphonyloxyundecyl)oestra-1,3,5(10)-triene (Example 24; 0.078 g.) in tetrahydrofuran (1 ml.) and the mixture was kept for 1 hour at laboratory temperature, neutralised with aqueous N-hydrochloric acid and extracted three times with ethyl acetate (10 ml. each time). The combined extracts were washed with water (3 ml.), dried and evaporated to dryness, and the residue was dissolved in methanol (3 ml.). Aqueous N-sodium hydroxide solution (1 ml.) was added and the mixture was kept at laboratory temperature for 18 hours, neutralised with aqueous N-hydrochloric acid and extracted three times with ethyl acetate (10 ml. each time). The combined extracts were washed with water (10 ml.), dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 4:1 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil 7α-(11-n-butylthioundecyl)oestra-1,3,5(10)-triene-3,17β-diol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. extractionextracted three times with ethyl acetate (10 ml
  2. washThe combined extracts were washed with water (3 ml.)
  3. customdried
  4. customevaporated to dryness
  5. dissolutionthe residue was dissolved in methanol (3 ml.)
  6. additionAqueous N-sodium hydroxide solution (1 ml.) was added
  7. waitthe mixture was kept at laboratory temperature for 18 hours
  8. extractionextracted three times with ethyl acetate (10 ml
  9. washThe combined extracts were washed with water (10 ml.)
  10. customdried
  11. customevaporated to dryness
  12. customthe residue was purified by chromatography on a silica gel column
  13. additiona 4:1 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-eed2ea71298746a2a7e5d515d38613a5
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

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