3-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-(2,2,2-trifluoro-ethoxy)-benzaldehyde → 1-ethyl-4,4,6-trimethyl-7-[2-(2,2,2-trifluoro-ethoxy)-5-vinyl-phenyl]-3,4-dihydro-1H-quinolin-2-one

HRID 1869555노트

반응식

HRID 1869555 반응식
[CH2:1]([Li])CCC.[CH2:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH3:32])=[C:15]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=3[O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH:21]=O)[CH:16]=2)[C:11]([CH3:34])([CH3:33])[CH2:10][C:9]1=[O:35])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH3:32])=[C:15]([C:18]3[CH:19]=[C:20]([CH:21]=[CH2:1])[CH:23]=[CH:24][C:25]=3[O:26][CH2:27][C:28]([F:30])([F:31])[F:29])[CH:16]=2)[C:11]([CH3:34])([CH3:33])[CH2:10][C:9]1=[O:35])[CH3:7]

참가 물질

5

반응물 2

HCID 579862973-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-(2,2,2-trifluoro-ethoxy)-benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 579863101-ethyl-4,4,6-trimethyl-7-[2-(2,2,2-trifluoro-ethoxy)-5-vinyl-phenyl]-3,4-dihydro-1H-quinolin-2-one수율 94%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

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온도
-10 °C

실험 절차

In accordance with Scheme 16, to a suspension of methyltriphenylphosphonium bromide (3.27 mmol, 1.17 g) in 7.5 mL THF was added a solution of n-butyllithium in hexanes (1.6 M, 3.27 mmol, 2.04 mL) at −40° C. The reaction was warmed to −10° C. and stirred for 30 min. The reaction mixture was cooled to −60° C. and then Compound 1D (0.14 mmol, 0.06 g), in 7.5 mL THF, was added dropwise. The yellow suspension was allowed to stir at r.t. overnight and then quenched by adding 1 mL H2O. It was extracted with EtOAc and was washed with brine. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo. The yellow oil thus obtained was then purified by column chromatography (3.5:1 hexanes/EtOAc) to obtain 1-ethyl-4,4,6-trimethyl-7-[2-(2,2,2-trifluoro-ethoxy)-5-vinyl-phenyl]-3,4-dihydro-1H-quinolin-2-one as a colorless thick gum (0.61 g, 94% yield).

후처리

  1. temperatureThe reaction mixture was cooled to −60° C.
  2. stirringto stir at r.t. overnight
  3. customquenched
  4. additionby adding 1 mL H2O
  5. extractionIt was extracted with EtOAc
  6. washwas washed with brine
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent was removed in vacuo
  11. customThe yellow oil thus obtained
  12. customwas then purified by column chromatography (3.5:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-6eb20adead9b41e1b9a3e4ec45244da3
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638533B2

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