Chloroform → 11beta-Chloro-17beta-hydroxy-7alpha-methyl-estr-4-en-3-one

HRID 900683Notes

Reaction equation

HRID 900683 reaction equation
[CH2:1]([C@@H:3]1[CH2:20][C:19]2[C@H:14]([CH2:15][CH2:16][C:17](=[O:21])[CH:18]=2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][C@@H]2F)([CH3:10])[C@@H:8]([OH:23])[CH2:7][CH2:6]1)C.C([Mg]Br)C.C([C@@H]1CC2[C@H](CCC(=O)C=2)[C@@H]2[C@@H]1[C@H]1[C@@](C[C@@H]2F)(C)C(=O)CC1)C.[CH:51]([Cl:54])(Cl)Cl>>[Cl:54][C@H:51]1[CH2:10][C@@:9]2([CH3:11])[C@@H:5]([CH2:6][CH2:7][C@@H:8]2[OH:23])[C@H:4]2[C@H:13]1[C@@H:14]1[C:19]([CH2:20][C@H:3]2[CH3:1])=[CH:18][C:17](=[O:21])[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 99016427alpha-Ethyl-11beta-fluoro-17beta-hydroxy-estr-4-en-3-oneHCID 691049877alpha-Ethyl-11beta-fluoro-estr-4-en-3,17-dioneHCID 178418443HCID 178418443, compound

Product 1

HCID 985836511beta-Chloro-17beta-hydroxy-7alpha-methyl-estr-4-en-3-one

Procedure

In analogy to Example 1 7α-Ethyl-11β-fluoro-17β-hydroxy-estr-4-en-3-one, using ethylmagnesium bromide instead of methylmagnesium bromide, is obtained; Fp. 115.1° C., [α]D20=+62,1° (in chloroform). The intermediate 7α-Ethyl-11β-fluoro-estr-4-en-3,17-dione shows Fp.=174.9° C. and [α]D20=+107,1° (chloroform).

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-5890cdf7e50c49cbbae6d71b65d9c14b
Source dataset
uspto-grants-2008_04
Patent number
US07361645B2

Reaction notes

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