Boron trifluoride → HCID 86733307, compound

HRID 1606373Notes

Reaction equation

HRID 1606373 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.B(F)(F)F.[C:29]([OH:32])(=[S:31])[CH3:30]>CCOCC>[C:29]([S:31][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])(=[O:32])[CH3:30]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 86733130HCID 86733130, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86733307HCID 86733307, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (450 mg.) in dry ether (4 ml.) and thioacetic acid (1 ml.) was treated with BF3 etherate (2 drops). The resulting yellow solution was stirred at room temperature for 20 minutes. The solution was partitioned between ethyl acetate (20 ml.) and water (20 ml.) and the aqueous layer was extracted with more ethyl acetate (20 ml.). The combined organic extracts were washed with water (2 × 20 ml.) and dried over sodium sulphate and evaporated to a yellow oil which was purified by preparative t.l.c., in ethyl acetate/petroleum ether (1:1) to give the title compound as a pale yellow foam. [α]D + 93° (c 0.56); Rf 0.15; N.M.R.:-7.65τ (CH3COS--); 6.16τ (2-- and 3--H).

Workup

  1. customThe solution was partitioned between ethyl acetate (20 ml.) and water (20 ml.)
  2. extractionthe aqueous layer was extracted with more ethyl acetate (20 ml.)
  3. washThe combined organic extracts were washed with water (2 × 20 ml.)
  4. dry with materialdried over sodium sulphate
  5. customevaporated to a yellow oil which
  6. customwas purified by preparative t.l.c

Sources & evidence

ORD record
ord-a0b6f3f364bf4b2e8aeec7d7e7385dd9
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

Loading…