Trifluoroacetic anhydride → 6-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1859811ノート

反応式

HRID 1859811 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[CH3:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[CH3:9])[C:13](=[O:15])[CH2:12][CH2:11][CH2:10]2

参加物

5

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 186264724-(3-Methoxy-4-methylphenyl)butanoic acid

生成物 1

HCID 113559636-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one収率 54.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 5.6 g (26.9 mmol) of 4-(3-methoxy-4-methylphenyl)butanoic acid in 100 mL of CH2Cl2 was cooled in ice and treated dropwise with 25 mL of trifluoroacetic anhydride. After stirring at 0° C. for 1 hour, the solution was diluted with Et2O and washed twice with 5% NaOH, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with CH2Cl2 gave 2.79 g (54.7% yield) of the product as a white solid, mp 104-107° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 191 (M+H+).

後処理

  1. washwashed twice with 5% NaOH
  2. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  3. waitleft the crude product
  4. washChromatography on silica gel, eluting with CH2Cl2

出典と根拠

ORDレコード
ord-845fbe76686048abbce0de3cb43ba391
出典データセット
uspto-grants-2003_03
特許番号
US06528535B2

反応ノート

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