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

HRID 883073

反応式

HRID 883073 の反応式
[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]

参加物

7

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-47d8fcc97d284dd3937d91c261d965f2
出典データセット
uspto-grants-2012_08
特許番号
US08236819B2

関連ノート

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