Potassium Carbonate → 3-Methyl-3-naphthalen-1-ylmethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

HRID 1053724노트

반응식

HRID 1053724 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([O:11][CH2:12][C:13]([CH3:15])=[CH2:14])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]1(B(O)O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[C:13]([CH3:15])([CH2:14][C:31]3[C:32]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:28]=[CH:29][CH:30]=3)[CH2:12][O:11][C:6]=2[CH:5]=1)=[O:16]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 251290454-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester

생성물 1

HCID 684828853-Methyl-3-naphthalen-1-ylmethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester수율 43%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 4-Iodo-3-(2-methyl-allyloxy)-benzoic acid methyl ester (455 mg, 1.37 mmol) in DMF (15 mL) were added Potassium carbonate (379 mg, 2.74 mmol), Tetrabutylammonium chloride (380 mg, 1.37 mmol), Palladium acetate (25.6 mg, 0.136 mmol) in DMF (5 mL) and 1-Naphthylboronic acid, (282 mg, 1.64 mmol) was submitted to microwave irradiation at 100° C. for 10 minutes and as the reaction was not completed at 150° C. for 15 minutes. The resulting mixture was filtered over silica, washed with water, dried over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded 196 mg (43%) of the title compound as a slightly brown oil.

후처리

  1. customirradiation at 100° C. for 10 minutes
  2. filtrationThe resulting mixture was filtered over silica
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7154eea300cb4007b345af83072114f1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394267B2

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