Dimethylformamide → (1R,4aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,7,10a-decahydrophenanthrene-1-carbonyl chloride

HRID 1627239

反応式

HRID 1627239 の反応式
[CH3:1][CH:2]([CH:4]1[CH:9]=[C:8]2[CH2:10][CH2:11][CH:12]3[C:17]([C:19](O)=[O:20])([CH3:18])[CH2:16][CH2:15][CH2:14][C:13]3([CH3:22])[CH:7]2[CH2:6][CH2:5]1)[CH3:3].P(Cl)(Cl)[Cl:24].CN(C=O)C>C1COCC1>[CH3:18][C@:17]1([C:19]([Cl:24])=[O:20])[CH:12]2[C@@:13]([CH3:22])([CH:7]3[C:8]([CH:10]=[CH:11]2)=[CH:9][CH:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6]3)[CH2:14][CH2:15][CH2:16]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 227277Dihydroabietic acid

生成物 1

HCID 88415966(1R,4aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,7,10a-decahydrophenanthrene-1-carbonyl chloride収率 93.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of dihydroabietic acid (1.0 eq. 9.95 mmol), phosphorous (III) chloride (1.1 eq. 10.95 mmol) and DMF (0.1 ml) is refluxed overnight in THF (20 ml). The reaction mass is filtered under suction and concentrated under vacuum to give 2.98 g (93%) yellow oil. The compound is used immediately for the next step without any purification.

後処理

  1. filtrationThe reaction mass is filtered under suction
  2. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-56121c6b026d4937a41bbe65d50eda61
出典データセット
uspto-grants-2014_07
特許番号
US08785502B2

関連ノート

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