Hydrochloric Acid → 21-Acetoxy-6-chloro-11beta-hydroxy-16alpha-methyl-1,4,6-pregnatriene-3,20-dione

HRID 2049152ノート

反応式

HRID 2049152 の反応式
Cl.[C:2]([O:5][CH2:6][C:7](=[O:31])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C@@H:23]([OH:27])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[CH2:18][CH2:19]2)[C@@H:14]([Cl:29])[CH2:13]3)[CH2:10][C@H:9]1[CH3:30])(=[O:4])[CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:2]([O:5][CH2:6][C:7](=[O:31])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C@@H:23]([OH:27])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:28])[CH:18]=[CH:19]2)[C:14]([Cl:29])=[CH:13]3)[CH2:10][C@H:9]1[CH3:30])(=[O:4])[CH3:3]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7052009321-Acetoxy-6alpha-chloro-11beta-hydroxy-16alpha-methyl-4-pregnene-3,20-dione

生成物 1

HCID 7058383021-Acetoxy-6-chloro-11beta-hydroxy-16alpha-methyl-1,4,6-pregnatriene-3,20-dione

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A hydrogen chloride stream is introduced into a solution of 1.0 g. of 21-acetoxy-6α-chloro-11β-hydroxy-16α-methyl-4-pregnene-3,20-dione in 100 ml. of dioxane for 30 minutes at 25° after adding 1.5 g. of dichlorodicyanobenzoquinone. The solution is then heated for 15 hours to 120°. After cooling, the solution is filtered, the filter cake washed with dichloromethane, and the filtrate evaporated under vacuum. The residue of the evaporation is chromatographed on silica gel. With 32-40% acetone-hexane, after recrystallization from acetone-diisopropyl ether, 380 mg. of 21-acetoxy-6-chloro-11β-hydroxy-16α-methyl-1,4,6-pregnatriene-3,20-dione is obtained.

後処理

  1. temperatureThe solution is then heated for 15 hours to 120°
  2. temperatureAfter cooling
  3. filtrationthe solution is filtered
  4. washthe filter cake washed with dichloromethane
  5. customthe filtrate evaporated under vacuum
  6. customThe residue of the evaporation
  7. customis chromatographed on silica gel
  8. customWith 32-40% acetone-hexane, after recrystallization from acetone-diisopropyl ether, 380 mg

出典と根拠

ORDレコード
ord-08990c1696d24517aa3f524ff9be6906
出典データセット
uspto-grants-1980_04
特許番号
US04196203

反応ノート

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