Sodium Fluoride → 3beta-Acetoxy-5alpha,6beta-dichloro-14alpha-fluoropregnan-20-one

HRID 894507

반응식

HRID 894507 반응식
[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@:7]([Cl:28])([C@H:8]([Cl:27])[CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[F:29]C(F)(F)C([O-])=O.[Na+].[F-].[Na+].FF>FC(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@:7]([Cl:28])([C@H:8]([Cl:27])[CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@@:11]3([F:29])[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 5235Sodium FluorideHCID 24524Fluorine2회HCID 517019Sodium TrifluoroacetateHCID 705691213beta-Acetoxy-5alpha,6beta-dichloropregnan-20-one

생성물 1

HCID 705694493beta-Acetoxy-5alpha,6beta-dichloro-14alpha-fluoropregnan-20-one

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6389Trichlorofluoromethane용매

실험 절차

3β-Acetoxy-5α,6β-dichloropregnan-20-one (1.4 g) was dissolved in fluorotrichloromethane (250 ml) and chloroform (200 ml) containing sodium trifluoroacetate (ca. 2 g) and sodium fluoride (ca. 2 g). The resulting solution was cooled to -78° and vigourously stirred, whereupon fluorine from four 750 cc bottles (10% v/v fluorine in nitrogen) was bubbled through the solution over a period of 8 hours. The reaction solution was then poured into aqueous sodium thiosulphate and the organic layer was separated, washed with water, dried over potassium carbonate and evaporated to dryness to yield crude 3β-acetoxy-5α,6β-dichloro-14α-fluoropregnan-20-one.

후처리

  1. temperatureThe resulting solution was cooled to -78°
  2. customwas bubbled through the solution over a period of 8 hours
  3. additionThe reaction solution was then poured into aqueous sodium thiosulphate
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over potassium carbonate
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-234168b7e3f6491997a2f83d137b1c78
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04284558

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