Pyridine → 3-Cyano-1-(furan-3-yl)-6-(trifluoromethanesulfonyloxy)naphthalene

HRID 741834

反応式

HRID 741834 の反応式
CCN([C:6]1[CH:11]=[CH:10][C:9]2[C:12]([CH3:17])=[CH:13][C:14]([O:16][C:8]=2[CH:7]=1)=O)CC.N1C=[CH:22][CH:21]=[CH:20][CH:19]=1.[S:24]([O:31]S(C(F)(F)F)(=O)=O)([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25].[NH4+:39].[Cl-].[CH2:41](Cl)Cl>>[C:41]([C:11]1[CH:10]=[C:9]([C:12]2[CH:13]=[CH:14][O:16][CH:17]=2)[C:8]2[C:7]([CH:6]=1)=[CH:22][C:21]([O:31][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])=[CH:20][CH:19]=2)#[N:39]

参加物

6

反応物 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 70504-Methyl-7-diethylaminocoumarinHCID 25517Ammonium ChlorideHCID 67749Trifluoromethanesulfonic anhydride

生成物 1

HCID 117933133-Cyano-1-(furan-3-yl)-6-(trifluoromethanesulfonyloxy)naphthalene

反応条件

温度
0 °C

実験手順

To a solution of the Naphthalene 1 (565 mg, 2.40 mmol) in CH2Cl2 (16 mL) at 0° C. was added pyridine (380 mg, 4.80 mmol, 389 μL) and triflic anhydride (813 mg, 2.88 mmol, 485 μL). The solution was stirred at 0° C. for 2.5 h and then poured into sat. aq. NH4Cl. The layers were separated and the aq. phase extracted with EtOAc (3×30 mL). The combined organic layers were washed with 5% aq. HCl, 5% aq. NaHCO3, brine, and dried over anhydrous MgSO4. Evaporation of the solvent gave a solid (810 mg) which was used directly in the next step.

後処理

  1. customThe layers were separated
  2. extractionthe aq. phase extracted with EtOAc (3×30 mL)
  3. washThe combined organic layers were washed with 5% aq. HCl, 5% aq. NaHCO3, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-00502421e23949cf8b6bee1b9f1c1767
出典データセット
uspto-grants-1996_09
特許番号
US05552437

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