2,2,2-Trifluoroethanol → Fluocortin

HRID 2072195Notes

Reaction equation

HRID 2072195 reaction equation
[F:1][C@@H:2]1[C:22]2[C@:17]([CH3:24])([CH:18]=[CH:19][C:20](=[O:23])[CH:21]=2)[C@@H:16]2[C@H:4]([C@H:5]3[C@:13]([CH3:26])([CH2:14][C@@H:15]2[OH:25])[C@@H:8]([C:9](=[O:12])[CH:10]=[O:11])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1.FC(F)(F)C[OH:31]>C(Cl)(Cl)Cl>[F:1][C@@H:2]1[C:22]2[C@:17]([CH3:24])([CH:18]=[CH:19][C:20](=[O:23])[CH:21]=2)[C@@H:16]2[C@H:4]([C@H:5]3[C@:13]([CH3:26])([CH2:14][C@@H:15]2[OH:25])[C@@H:8]([C:9](=[O:12])[C:10]([OH:31])=[O:11])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1

Participants

4

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 86735083HCID 86735083, compound

Product 1

HCID 22875828Fluocortin

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.0 g. of 6α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-al is reacted, under the conditions described in Example 46 but with 2,2,2-trifluoroethanol, thus obtained the 2,2,2-trifluoroethyl ester of 6α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-oic acid, m.p. 192.9° C. [α]D25 = +130° (chloroform). UV: ε242 = 17,000 (methanol).

Sources & evidence

ORD record
ord-b9219958f5ad4ce1bb60ba2ae4d5f3bb
Source dataset
uspto-grants-1977_09
Patent number
US04049804

Reaction notes

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