Hexane → Ammonium Hydroxide

HRID 1739786

Reaktionsgleichung

Reaktionsgleichung von HRID 1739786
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH2:6]([N:8]1[CH2:17][CH2:16][C@@:15]2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[C@@H:10]([CH2:11][CH2:12][C:13](=O)[CH2:14]2)[CH2:9]1)[CH3:7].[CH3:27][CH2:28][CH2:29]CCC>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[NH4+:8].[OH-:24].[CH:1](=[C:13]1[CH2:12][CH2:11][C@@H:10]2[C@:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)([CH2:16][CH2:17][N:8]([CH2:6][CH3:7])[CH2:9]2)[CH2:14]1)[C:2]1[CH:29]=[CH:28][CH:27]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 8058HexaneHCID 10517409(+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinoneHCID 178418339Butyllithium

Produkt 2

HCID 14923Ammonium HydroxideHCID 86754628(+/-)-trans-6-Benzylidene-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)isoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70671Benzyltriphenylphosphonium chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

9.9 ml (13.9 mmol) of a 1.4 M solution of n-butyllithium in hexane were added dropwise, under a nitrogen atmosphere and at room temperature, to a suspension of 5.4 g (13.9 mmol) of benzyltriphenylphosphonium chloride in 30 ml of dry THF. The reaction mixture was stirred for 1 h, then a solution of 1 g (3.5 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinone in 10 ml of dry THF was added. The reaction mixture was refluxed 4 h, then cooled and poured onto water and the aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 0.94 g of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed 4 h
  2. temperaturecooled
  3. additionpoured onto water
  4. extractionthe aqueous phase was extracted with AcOEt
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customthe solvent removed in vacuo
  7. customThe crude reaction mixture
  8. customwas purified by flash chromatography
  9. washeluting with a mixture CH2Cl2 /MeOH/conc

Quellen und Nachweise

ORD-Eintrag
ord-8873cc4ed8fb4a249b44cb7f47806857
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05968949

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