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

HRID 259224

反応式

HRID 259224 の反応式
[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].C(Cl)(Cl)Cl.[F:33]C(F)(F)C([O-])=O.[Na+].FF>FC(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:33])[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 6212ChloroformHCID 24524Fluorine2 回HCID 517019Sodium Trifluoroacetate2 回HCID 705691213beta-Acetoxy-5alpha,6beta-dichloropregnan-20-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 6389Trichlorofluoromethane溶媒

実験手順

3β-Acetoxy-5α,6β-dichloropregnan-20-one (1.4g) was dissolved in fluorotrichloromethane (250 ml) and chloroform (200 ml) containing sodium trifluoroacetate (ca. 2g) and sodium fluoride (ca. 2g). 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.

後処理

  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

出典と根拠

ORDレコード
ord-3c3ad565cd7d4aa7871d8411fd71edfe
出典データセット
uspto-grants-1977_07
特許番号
US04036864

関連ノート

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