Hexane → 1-(6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone

HRID 1582087ノート

反応式

HRID 1582087 の反応式
[CH2:1]([Li])CCC.CCCCCC.CCOC(C(P(OCC)(OCC)=O)F)=O.[CH2:27]([N:29]1[C:38]2[C:33](=[CH:34][C:35]([CH:42]([CH3:44])[CH3:43])=[CH:36][C:37]=2[C:39](=[O:41])[CH3:40])[C:32]([CH3:46])([CH3:45])[CH2:31][CH2:30]1)[CH3:28]>C1COCC1>[CH:42]([C:35]1[CH:34]=[C:33]2[C:38](=[C:37]([C:39](=[O:41])[CH3:40])[CH:36]=1)[N:29]([CH2:27][CH2:28][CH3:1])[CH2:30][CH2:31][C:32]2([CH3:45])[CH3:46])([CH3:43])[CH3:44]

参加物

6

反応物 4

HCID 8058HexaneHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 227198241-(1-Ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone2 回HCID 178418339Butyllithium

生成物 1

HCID 227198321-(6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of a 1.6 M solution of n-butyl lithium in hexane (3.33 ml, 5.33 mmol) and 20 ml of anhydrous THF under argon at −78° C. was slowly added triethyl-2-fluoro-2-phosphonoacetate (1.29 g, 5.33 mmol). After 40 minutes at −78° C., a solution of 1-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanone (Intermediate 12, 497 mg, 1.33 mmol) in 4 ml THF was added by cannula. The resulting mixture was stirred at −78° C. for 10 minutes, allowed to warm up to room temperature, and then heated to 80° C. for 12 hours. The reaction was quenched with saturated NH4Cl and product was extracted with ethyl ether. The extract was washed with water, and brine, dried over Na2SO4, concentrated in vacuo, and the residue was purified by column chromatography using 2% ethyl acetate in hexane to yield the title compound as a yellow oil.

後処理

  1. customat −78° C.
  2. temperatureto warm up to room temperature
  3. temperatureheated to 80° C. for 12 hours
  4. customThe reaction was quenched with saturated NH4Cl and product
  5. extractionwas extracted with ethyl ether
  6. washThe extract was washed with water, and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-30a0323590c541eeb19c9d9cf1e8e806
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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