2-Propanethiol → HCID 86733466, compound

HRID 1077008Notes

Reaction equation

HRID 1077008 reaction equation
[CH3:1][CH:2]([SH:4])[CH3:3].[Na].Br[CH2:7][C:8](=[O:30])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:29])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1>CC(O)C.C1(C)C=CC=CC=1>[OH:29][C@@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([CH2:15][CH2:14][C@@H:13]3[C@@H:23]2[C:24](=[O:28])[CH2:25][C@@:26]2([CH3:27])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C:8](=[O:30])[CH2:7][S:4][CH:2]([CH3:3])[CH3:1])[CH2:17]1

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 5360545SodiumHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Product 1

HCID 86733466HCID 86733466, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

Propane-2-thiol (1.3 ml.) was added to a warm solution of sodium (0.6 g.) in a mixture of propan-2-ol (25 ml.) and toluene (30 ml.). 21-Bromo-3α-hydroxy-5α-pregnane-11,20 -dione (0.7 g.) was then added and the mixture was gently refluxed for 2 hr. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residual foam was purified by preparative t.l.c. (CHCl3) to give title compound (0.2 g.) as a white foam, [α]D + 67° (c 1.3).

Workup

  1. temperaturethe mixture was gently refluxed for 2 hr
  2. customThe mixture was then partitioned between water and ether
  3. washthe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residual foam was purified by preparative t.l.c

Sources & evidence

ORD record
ord-c625535119d8465881d728ea4baf0376
Source dataset
uspto-grants-1976_05
Patent number
US03959260

Reaction notes

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