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

반응식

HRID 1627239 반응식
[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

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 227277Dihydroabietic acid

생성물 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 chloride수율 93.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-56121c6b026d4937a41bbe65d50eda61
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785502B2

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