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

Reaktionsgleichung

Reaktionsgleichung von HRID 1627239
[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

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 227277Dihydroabietic acid

Produkt 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 chlorideAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-56121c6b026d4937a41bbe65d50eda61
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785502B2

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