HCID 10664064, compound → HCID 10686415, compound

HRID 361316Notes

Reaction equation

HRID 361316 reaction equation
[CH2:1]([C@H:4]1[C@:21]2(O)[C@H:16]([CH2:17][CH2:18][C:19](=[O:23])[CH2:20]2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:24])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3]>CC(C)=O.O>[CH2:1]([C@H:4]1[C:21]2[C@H:16]([CH2:17][CH2:18][C:19](=[O:23])[CH:20]=2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:24])[CH2:9][CH2:8]3)[CH2:5]1)[C:2]#[CH:3]

Participants

4

Reactant 1

HCID 10664064HCID 10664064, compound

Product 1

HCID 10686415HCID 10686415, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

6β-Propargyl-5α-hydroxyestrane-3,17-dione (11). The 6β-propargyl triol 9 (0.6 mmol) was dissolved in acetone (30 ml) and cooled to 4° C. followed by dropwise addition of Jone's reagent until the solution turned light brown. The reaction mixture was stirred at 4° C. for approximately 5 minutes, was diluted with water, extracted with ethyl acetate, washed (5% NaHCO3, brine, water) and dried, The ethyl acetate was evaporated in vacuo and the product obtained was purified by column chromatography to yield the dione 11 in 90% yield: m.p. 186°-188° C.; 1H-NMR (CDCl3) δ 0.91 (s, 3H, 18-CH3), 2.65 (d, 1H, 6-H).

Workup

  1. additionfollowed by dropwise addition of Jone's reagent until the solution
  2. extractionextracted with ethyl acetate
  3. washwashed (5% NaHCO3, brine, water)
  4. customdried
  5. customThe ethyl acetate was evaporated in vacuo
  6. customthe product obtained
  7. customwas purified by column chromatography
  8. customto yield the dione 11 in 90% yield

Sources & evidence

ORD record
ord-9904bcca5583405ba473ff0af70d471e
Source dataset
uspto-grants-1999_02
Patent number
US05866558

Reaction notes

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