Potassium Carbonate → (4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester

HRID 1468330노트

반응식

HRID 1468330 반응식
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[CH:12]=[C:11]([CH2:20]Cl)[C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1[CH2:27][O:26][CH2:25]C1.CO.C([O-])([O-])=[O:31].[K+].[K+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:25][O:26][C:27](=[O:31])[CH2:20][C:11]1[C:10]([CH3:22])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[CH:12]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 21899815MeOH tetrahydrofuranHCID 593265471-Benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene

생성물 1

HCID 59326535(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester수율 28%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

실험 절차

To a stirred solution of 1-benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene (18.5 g, 58.9 mmol) in a THF-methanol mixture (2:3; 500 mL) was added K2CO3 (8.94 g, 64.7 mmol) and PdCl2(PPh3)2 (2.06 g, 2.96 mmol) at room temperature. The solution was degassed by purging with argon for 5 minutes. The reaction mixture was stirred under a balloon of carbon monoxide overnight at room temperature. After this time, the reaction progress was monitored by TLC (5% ethyl acetate in hexanes). The reaction mixture was concentrated, and the obtained crude residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude product. Silica gel chromatography (100-200 mesh, 5% ethyl acetate-hexanes) yielded (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (5.5 g, 28%) as a pale yellow solid. MS calcd. for C21H20FO3 [(M+H)+] 339, obsd. 339.0.

후처리

  1. customThe solution was degassed
  2. customby purging with argon for 5 minutes
  3. concentrationThe reaction mixture was concentrated
  4. customthe obtained crude residue
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a crude product

출처 및 근거

ORD 기록
ord-34bda5a6354642edb962bb43a682968d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000044B2

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