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

HRID 339169ノート

反応式

HRID 339169 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f313669e91084be78c0365b7cc48a292
出典データセット
uspto-grants-2014_11
特許番号
US08889906B2

反応ノート

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