Water → 6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

HRID 2103334노트

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HRID 2103334 반응식
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN1C(=O)CCC1.CCOC(C)=O>[C:13]1([S:19][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 149151166-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

생성물 1

HCID 149576696-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one수율 94.31%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
80 °C

실험 절차

A solution of 6-fluoro-3,4-dihydro-2H-naphthalen-1-one (5.51 g, 33.56 mmol), benzenethiol (4.07 g, 3.79 mL, 36.92 mmol) and K2CO3 (9.28 g, 67.12 mmol) in 50 mL of N-methyl pyrrolidinone (NMP) was heated to 80° C. under argon and stirred at 80° C. for 2 hours. The reaction mixture was poured into 500 mL of water and diluted with 300 mL of EtOAc. The layers were separated and the aqueous layer was extracted twice with 250 mL of EtOAc. The combined organic layers were washed with water, saturated brine, and then dried over MgSO4. The solvent was removed under reduced pressure to yield an oil which was eluted through silica gel using hexanes/EtOAc (9:1). Removal of solvent under reduced pressure provided 8.05 g (31.65 mmol, 94.31%) of 6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one as a pale yellow oil. MS: 255 (M+H)+.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with 250 mL of EtOAc
  3. washThe combined organic layers were washed with water, saturated brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customto yield an oil which
  7. washwas eluted through silica gel
  8. customRemoval of solvent under reduced pressure

출처 및 근거

ORD 기록
ord-bb47c6fe340d4e01889dbdd0197517c8
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576103B2

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