Hexane → (E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enal

HRID 1582096ノート

反応式

HRID 1582096 の反応式
[CH2:1](OP(CC(C)=CC(OCC)=O)(OCC)=O)C.C([Li])CCC.CCCCCC.[CH2:29]([N:31]1[C:40]2[C:35](=[CH:36][C:37]([CH:47]([CH3:49])[CH3:48])=[CH:38][C:39]=2/[C:41](/[CH3:46])=[C:42](/[F:45])\[CH:43]=[O:44])[C:34]([CH3:51])([CH3:50])[CH2:33][CH2:32]1)[CH3:30]>C1COCC1.CN1CCCN(C)C1=O>[F:45]/[C:42](=[C:41](/[C:39]1[CH:38]=[C:37]([CH:47]([CH3:48])[CH3:49])[CH:36]=[C:35]2[C:40]=1[N:31]([CH2:29][CH2:30][CH3:1])[CH2:32][CH2:33][C:34]2([CH3:50])[CH3:51])\[CH3:46])/[CH:43]=[O:44]

参加物

7

反応物 4

HCID 8058HexaneHCID 2773818Ethyl 4-(diethoxyphosphoryl)-3-methylcrotonateHCID 22719813(E)-3-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-but-2-enal2 回HCID 178418339Butyllithium

生成物 1

HCID 22719829(E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-enal

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
0 °C

実験手順

To a solution of ethyl 4-(diethoxyphosphoryl)-3-methyl-but-2-enoate (210 mg, 0.80 mmol), 10 ml of anhydrous THF, and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.12 ml) under argon at −78° C. was slowly added a 1.6 M solution of n-butyl lithium and hexane (0.52 ml, 0.84 mmol). The resulting mixture was stirred at −78° C. for 30 minutes before a solution of (E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-but-2-enal (Intermediate 21, 87 mg, 0.27 mmol) and 3 ml THF was added by cannula. The resulting mixture was stirred at 0° C. for 1 h. The reaction was quenched with saturated NH4Cl, and the product was extracted with ethyl ether. The extract was washed with water, and brine, and dried over Na2SO4. The solution was filtered and concentrated in vacuo. The residue was purified by column chromatography using 5% ethyl acetate in hexane to yield the title compound as a bright yellow oil.

後処理

  1. additionwas added by cannula
  2. customThe reaction was quenched with saturated NH4Cl
  3. extractionthe product was extracted with ethyl ether
  4. washThe extract was washed with water, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-2a40f2ded9c74ebe8ebbd971e9f9849c
出典データセット
uspto-grants-2004_05
特許番号
US06734193B1

反応ノート

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