Diethyl Ether → 7-(5-Acetyl-2-trifluoromethoxy-phenyl)-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1h-quinolin-2-one

HRID 883073

반응식

HRID 883073 반응식
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH3:26])=[C:10]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=3[O:21][C:22]([F:25])([F:24])[F:23])[CH:16]=[O:17])[CH:11]=2)[C:6]([CH3:28])([CH3:27])[CH2:5][C:4]1=[O:29])[CH3:2].[CH3:30][Mg]Br.CCOCC.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.ClCCl>[C:16]([C:15]1[CH:18]=[CH:19][C:20]([O:21][C:22]([F:23])([F:24])[F:25])=[C:13]([C:10]2[CH:11]=[C:12]3[C:7]([C:6]([CH3:28])([CH3:27])[CH2:5][C:4](=[O:29])[N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[CH3:26])[CH:14]=1)(=[O:17])[CH3:30]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 112234493-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-trifluoromethoxy-benzaldehydeHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 686663477-(5-Acetyl-2-trifluoromethoxy-phenyl)-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1h-quinolin-2-one수율 75%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of Compound 2A (270 mg, 0.66 mmol) in 3 mL of dry THF was cooled to −78° C. and treated with a 3M solution of methyl magnesium bromide in ether (0.24 mL, 0.73 mmol). The reaction mixture was allowed to slowly warm to room temperature where it was quenched with 10 mL of a saturated ammonium chloride solution. The reaction mixture was then passed through a 10 mL SPE (solid phase extraction) column which was further washed with dichloromethane. The eluant was collected and stripped to give crude alcohol which was then dissolved in dichloromethane and treated with Dess-Martin reagent (336 mg, 0.79 mmol) and stirred at room temperature overnight. The reaction was quenched with 4 mL of saturated sodium thiosulfate solution and 4 mL of saturated sodium bicarbonate solution, the reaction mixture was stirred until clear. The reaction mixture was passed through another SPE and eluted with dichloromethane, removal of solvent yielded crude ketone which was purified with flash chromatography (25% EtOAc/hexane) to yield 207 mg (75%) of the desired product (Compound 19A) and a white solid. MS (electrospray): mass calculated for C23H24F3NO3, 419.17; m/z found 420.2 [M+H]+.

후처리

  1. customwas quenched with 10 mL of a saturated ammonium chloride solution
  2. extractionThe reaction mixture was then passed through a 10 mL SPE (solid phase extraction) column which
  3. washwas further washed with dichloromethane
  4. customThe eluant was collected
  5. customto give crude alcohol which
  6. customThe reaction was quenched with 4 mL of saturated sodium thiosulfate solution and 4 mL of saturated sodium bicarbonate solution
  7. stirringthe reaction mixture was stirred until clear
  8. washeluted with dichloromethane, removal of solvent
  9. customyielded crude ketone which
  10. customwas purified with flash chromatography (25% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-47d8fcc97d284dd3937d91c261d965f2
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236819B2

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