Sodium Acetate → 4-Acetoxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester

HRID 1644735

반응식

HRID 1644735 반응식
[CH3:1][O:2][C:3](=[O:18])[C:4](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[CH:5]([CH3:9])[C:6]([OH:8])=O.[C:19]([O-])(=[O:21])[CH3:20].[Na+]>C(OC(=O)C)(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([CH3:9])=[C:6]([O:8][C:19](=[O:21])[CH3:20])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[CH:10]=1)=[O:18]

참가 물질

5

반응물 2

HCID 517045Sodium AcetateHCID 667755872-(4-Fluoro-benzylidene)-3-methyl-succinic acid 1-methyl ester

생성물 1

HCID 593508484-Acetoxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester수율 34%

시약·촉매·용매 2

HCID 7918Acetic Anhydride용매HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

To a solution of crude 2-(4-fluoro-benzylidene)-3-methyl-succinic acid 1-methyl ester (approximately 49 g, 0.196 mol) in acetic anhydride (490 mL) was added sodium acetate (32.15 g, 0.392 mol) in one portion. The reaction mixture was stirred at 150° C. for 3 hours. After this time, the reaction mixture was cooled to room temperature, then stirred overnight. Acetic anhydride was removed in vacuo, providing a viscous brown oil. This crude product was dissolved in ethyl acetate. The resulting solution was washed with a saturated, aqueous ammonium chloride solution. The organic phase was dried over Na2SO4, filtered, and concentrated. Flash chromatography (Analogix SuperFlash™ 10% ethyl acetate in hexane) gave 18.4 g (34%) of 4-acetoxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester as a yellow oil.

후처리

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. stirringstirred overnight
  3. customAcetic anhydride was removed in vacuo
  4. customproviding a viscous brown oil
  5. washThe resulting solution was washed with a saturated, aqueous ammonium chloride solution
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-17889a430be241ea8277e3a6dd473dbc
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124629B2

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