2-Chloroethanol → Fluocortin

HRID 2072192Notes

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.ClCC[OH:31]>>[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

Reactant 2

HCID 342-Chloroethanol

HCID 86735083HCID 86735083, compound

Product 1

HCID 22875828Fluocortin

Procedure

5.0 g. of 6α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-al is reacted, under the conditions set forth in Example 46, but with 2-chloroethanol in place of 2-fluoroethanol, and then worked up. The crude product is chromatographed on silica gel. With 25-29% acetone-hexane, 2.19 g. of the 2-chloroethyl ester of 6α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-oic acid is obtained, m.p. 174.8° C. [α]D25 = +135°. UV: ε242 = 17,100 (methanol).

Workup

customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record: ord-243c49c9ce4f44848d06c4a732eaeee0
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04049804

Reaction notes

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