Diethyl Ether → HCID 86733299, compound

HRID 1606364Notes

Reaction equation

HRID 1606364 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.CCOCC.[C:30]([CH2:32][CH2:33][OH:34])#[N:31].C(=O)(O)[O-].[Na+]>B(F)(F)F.CCOCC.C(OCC)(=O)C>[C:30]([CH2:32][CH2:33][O:34][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])#[N:31]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8011HydracrylonitrileHCID 516892Sodium BicarbonateHCID 86733130HCID 86733130, compound

Product 1

HCID 86733299HCID 86733299, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (2 g), dry ether (50 ml) and 2-cyanoethanol (10 ml.) were sirred at room temperature until the solid had dissolved. Boron trifluoride diethyl etherate (10 drops) was added. After 2 hours at room temperature a further quantity of etherate (10 drops) was added. After 1 hour further etherate (10 drops) was added and after a further hour, the mixture was neutralised with saturated sodium bicarbonate solution, ethyl acetate (50 ml.) added and the organic layer washed with water (3 × 200 ml.). The washed solution was dried over anhydrous sodium sulphate and evaporated to a white foam which was purified by preparative T.L.C. using ethyl acetate. The main band (Rf 0.4) gave the title compound (740 mg;) m.p. 194°-196°C. [α]D + 85° .

Workup

  1. customwere sirred at room temperature until the solid
  2. dissolutionhad dissolved
  3. additionAfter 2 hours at room temperature a further quantity of etherate (10 drops) was added
  4. additionAfter 1 hour further etherate (10 drops) was added and after a further hour
  5. additionadded
  6. washthe organic layer washed with water (3 × 200 ml.)
  7. dry with materialThe washed solution was dried over anhydrous sodium sulphate
  8. customevaporated to a white foam which
  9. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-08aa7627f3a340b0ae192548cc1e16d6
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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