Perfluoro-1-butanesulfonyl fluoride → HCID 69916400, compound

HRID 1837276Notes

Reaction equation

HRID 1837276 reaction equation
N12CCCN=C1CCCCC2.[F:12]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.[Cl:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C@@H:39]1[CH2:56][C:55]2[C@H:50]([CH2:51][CH2:52][C:53](=[O:57])[CH:54]=2)[C@@H:49]2[C@@H:40]1[C@H:41]1[C@@:45]([CH2:47][CH:48]2O)([CH3:46])[C:44](=[O:59])[CH2:43][CH2:42]1>C(OCC)(=O)C>[Cl:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C@@H:39]1[CH2:56][C:55]2[C@H:50]([CH2:51][CH2:52][C:53](=[O:57])[CH:54]=2)[C@@H:49]2[C@@H:40]1[C@H:41]1[C@@:45]([CH2:47][C@@H:48]2[F:12])([CH3:46])[C:44](=[O:59])[CH2:43][CH2:42]1

Participants

5

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69917869HCID 69917869, compound

Product 1

HCID 69916400HCID 69916400, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3.3 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene and, drop by drop, 4 ml of perfluorobutane-1-sulfonic acid fluoride are added to 6.7 g of 7α-(9-chlorononyl)-11-hydroxy-estr-4-ene-3,17-dione in 35 ml of ethyl acetate at 0° C. After 2 hours, it is diluted with ethyl acetate, washed several times with 2N hydrochloric acid and neutralized with saturated sodium bicarbonate solution and water. The crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient. Yield: 6.2 g of 7α-(9-chlorononyl)-11β-fluor-estr-4-ene-3,17-dione as an oil.

Workup

  1. washwashed several times with 2N hydrochloric acid
  2. customThe crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-454e53627cee41b69c44eead3e4cf5b1
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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