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

HRID 259224
Notes
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Reaction equation

HRID 259224 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6389TrichlorofluoromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3c3ad565cd7d4aa7871d8411fd71edfe
Source dataset
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04036864

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes