Methanol → Methyl 6-cyanonaphthalene-2-carboxylate

HRID 325062ノート

反応式

HRID 325062 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:47][OH:48].CN([CH:52]=[O:53])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:47][O:48][C:52]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:9]=1)=[O:53]

参加物

7

反応物 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 155418226-Cyano-2-naphthyl trifluoromethanesulfonate

生成物 1

HCID 12433083Methyl 6-cyanonaphthalene-2-carboxylate収率 50%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
60 °C

実験手順

To a solution of trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester from Example 95 (1.50 g, 4.98 mmol) in 20 mL of anhydrous DMF was added palladium(II) acetate (33.53 mg, 0.15 mmol), triphenylphosphine (78.36 mg, 0.30 mmol), triethylamine (1.39 mL, 9.96 mmol) and 5 mL of methanol. This mixture was purged with carbon monoxide for ten minutes. The reaction mixture was then placed under balloon pressure of carbon monoxide and heated to 60° C. for 16 hours. The mixture was then diluted with brine, extracted with EtOAc (3×100 mL), extracts washed with 1N HCl (2×100 mL), dried over MgSO4, and concentrated under reduced pressure. Flash chromatography (hexane to 20% EtOAc/hexane) afforded the desired product as a white solid (525 mg, 50%).

後処理

  1. customThis mixture was purged with carbon monoxide for ten minutes
  2. additionThe mixture was then diluted with brine
  3. extractionextracted with EtOAc (3×100 mL)
  4. washextracts washed with 1N HCl (2×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4b46675ff31b458c9771bf2ace0025cd
出典データセット
uspto-grants-2001_04
特許番号
US06221914B1

反応ノート

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