Water → HCID 15513552, compound

HRID 968184Notes

Reaction equation

HRID 968184 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][CH:16]2[OH:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:21])[CH2:6][CH2:5]1.O>C(#N)C.[Cu](Br)Br>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:21])=[CH:8][C:9]=1[CH2:10][CH2:11]2

Participants

5

Reactant 2

HCID 962WaterHCID 23396842HCID 23396842, compound

Product 1

HCID 15513552HCID 15513552, compound

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)Catalyst2×HCID 6342AcetonitrileSolvent

Procedure

43.55 g of 11β-fluoro-4-estren-17-ol-3-one (150 mmol, Tetrahedron Letters 1995, 2611) is suspended in 1500 ml of acetonitrile, 50 g of copper(II) bromide is added, and it is stirred at room temperature. After 16 hours, additional copper(II) bromide is added in three portions (25 g, 12 g, 6 g) within 6 hours, and finally stirred for another 6 hours at room temperature. The reaction mixture is cooled in an ice bath, mixed with 500 ml of water and extracted with ethyl acetate. The organic phase is mixed with a little methanol, washed with saturated bicarbonate solution and common salt solution and dried with sodium sulfate. After concentration by evaporation, the substance crystallizes out, yield 30.8 g (71% of theory), flash point 233-234° C.

Workup

  1. stirringfinally stirred for another 6 hours at room temperature
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. extractionextracted with ethyl acetate
  4. additionThe organic phase is mixed with a little methanol
  5. washwashed with saturated bicarbonate solution and common salt solution
  6. dry with materialdried with sodium sulfate
  7. concentrationAfter concentration
  8. customby evaporation
  9. customthe substance crystallizes out

Sources & evidence

ORD record
ord-7e1d6c0d46bf41239368e55912e886be
Source dataset
uspto-grants-2005_10
Patent number
US06958327B1

Reaction notes

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