2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68127264, compound

HRID 1076281Notes

Reaction equation

HRID 1076281 reaction equation
[F:1][C@@H:2]1[C:23]2[C@:18]([CH3:25])([CH2:19][CH2:20][C:21](=[O:24])[CH:22]=2)[C@@H:17]2[C@H:4]([C@H:5]3[C@:14]([CH3:26])([CH2:15][CH2:16]2)[C@@H:8]([C:9](=[O:13])[C:10]([OH:12])=[O:11])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[F:1][C@@H:2]1[C:23]2[C@:18]([CH3:25])([CH:19]=[CH:20][C:21](=[O:24])[CH:22]=2)[C@@H:17]2[C@H:4]([C@H:5]3[C@:14]([CH3:26])([CH2:15][CH2:16]2)[C@@H:8]([C:9](=[O:13])[C:10]([OH:12])=[O:11])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68125198HCID 68125198, compound

Product 1

HCID 68127264HCID 68127264, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.0 g. of the butyl ester of 6α-fluoro-3,20-dioxo-16α-methyl-4-pregnene-21-oic acid in 30 ml. of benzene is combined with 1.0 g. of 2,3-dichloro-5,6-dicyanobenzoquinone and heated to the boiling point for 24 hours. The solution is then filtered and concentrated under vacuum. The residue is chromatographed with an acetone/hexane gradient on silica gel. After recrystallization from acetone/hexane, 465 mg. of the butyl ester of 6α-fluoro-3,20-dioxo-16α-methyl-1,4-pregnadiene-21-oic acid is obtained as a viscous oil. [α]D25 = + 108° (chloroform). UV: ε241 = 17,900 (methanol).

Workup

  1. filtrationThe solution is then filtered
  2. concentrationconcentrated under vacuum
  3. customThe residue is chromatographed with an acetone/hexane gradient on silica gel
  4. customAfter recrystallization from acetone/hexane, 465 mg

Sources & evidence

ORD record
ord-2ed269ec8908418d84864af3cbe68319
Source dataset
uspto-grants-1976_05
Patent number
US03956347

Reaction notes

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