Ethanethiol → HCID 86733316, compound

HRID 1606386Notes

Reaction equation

HRID 1606386 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[CH2:25]([SH:27])[CH3:26].B(F)(F)F.C(=O)(O)[O-].[K+]>CCOCC>[CH2:25]([S:27][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:1])[CH3:26]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 6356Boron trifluorideHCID 516893Potassium BicarbonateHCID 86733130HCID 86733130, compound

Product 1

HCID 86733316HCID 86733316, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (50 mg.) in dry ether was treated with ethanethiol (0.8 mls.) and BF3 etherate (3 drops). The reaction mixture was stirred at room temperature for 20 minutes; then ether (5 mls.) and potassium bicarbonate solution (10%, 2.5 ml.) were added. The ether layer was evaporated to about 5 mls. and purified by preparative t.l.c. in ethyl acetate/petroleum ether (2:1) to give a colourless oil (200 mgs.) which was triturated with acetone and petroleum ether to give the title compound (174mg); fine white crystals; m.p. 170°-173°; [α]D + 93° (c 0.6).

Workup

  1. customThe ether layer was evaporated to about 5 mls
  2. customand purified by preparative t.l.c
  3. customin ethyl acetate/petroleum ether (2:1) to give a colourless oil (200 mgs.) which
  4. customwas triturated with acetone and petroleum ether

Sources & evidence

ORD record
ord-fc55a60f29be4df29602642de941b2e9
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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