Hexane → Ammonium Hydroxide

HRID 1739786

반응식

HRID 1739786 반응식
[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

참가 물질

7

반응물 3

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

생성물 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

시약·촉매·용매 2

HCID 70671Benzyltriphenylphosphonium chloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8873cc4ed8fb4a249b44cb7f47806857
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968949

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