2-Chloroethanol → HCID 70634744, compound

HRID 2072194Notes

Reaction equation

HRID 2072194 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@:16]2([F:25])[C@H:4]([C@H:5]3[C@:13]([CH3:27])([CH2:14][C@@H:15]2[OH:26])[C@@H:8]([C:9](=[O:12])[CH:10]=[O:11])[C@H:7]([CH3:28])[CH2:6]3)[CH2:3]1.ClCC[OH:32]>>[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@:16]2([F:25])[C@H:4]([C@H:5]3[C@:13]([CH3:27])([CH2:14][C@@H:15]2[OH:26])[C@@H:8]([C:9](=[O:12])[C:10]([OH:32])=[O:11])[C@H:7]([CH3:28])[CH2:6]3)[CH2:3]1

Participants

3

Reactant 2

HCID 342-ChloroethanolHCID 22802075HCID 22802075, compound

Product 1

HCID 70634744HCID 70634744, compound

Procedure

3.3 g. of 6α,9α-difluoro-11βhydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-al is reacted under the conditions described in Example 46, but with 2-chloroethanol. The crude product is chromatographed on silica gel. With 25-27% acetone-hexane, after recrystallization from acetone/hexane, 1.11 g. of the 2-chloroethyl ester of 6α,9α-difluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-oic acid is obtained; m.p. 172.0° C. [α]D25 =+123° (chloroform). UV: ε238 = 17,200 (methanol).

Workup

  1. customThe crude product is chromatographed on silica gel
  2. customWith 25-27% acetone-hexane, after recrystallization from acetone/hexane, 1.11 g

Sources & evidence

ORD record
ord-c8ace895e7c649668fa886c9dcbcebb6
Source dataset
uspto-grants-1977_09
Patent number
US04049804

Reaction notes

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