Lithium Chloride → Methyl 1,1-dimethyl-3-phenyl-1H-indene-5-carboxylate

HRID 53280

반응식

HRID 53280 반응식
[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[C:4](OS(C(F)(F)F)(=O)=O)=[CH:3]1.[Cl-].[Li+].[C:26]1([Sn](CCCC)(CCCC)CCCC)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:3]1

참가 물질

7

반응물 3

HCID 433294Lithium ChlorideHCID 607632TributylphenyltinHCID 19034466Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate

생성물 1

HCID 19034436Methyl 1,1-dimethyl-3-phenyl-1H-indene-5-carboxylate수율 83.1%

시약·촉매·용매 3

HCID 11773Triphenylarsine촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

실험 절차

Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate (580 mg, 1.86 mmol ), tris(dibenzylideneacetone)dipalladium (0) (Pd2 dba3, 17 mg, 0.02 mmol), triphenylarsine (46 mg, 0.15 mmol), lithium chloride (240 mg, 5.59 mmol) and phenyltributyltin (680 mg, 1.86 mmol) in 5 mL of 2-methyl pyrrolidinone were stirred at 55° C. for 1.5 days. The mixture was diluted with water (30 mL), and extracted with ethyl ether (30 mL×3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5) to give 0.43 g (83% yield) of the title compound as a white solid; 1H-NMR (CDCl3) δ1.41 (s, 6H), 3.91 (s, 3H), 6.48 (s, 1H), 7.39-7.62 (m, 6H), 7.99 (d, J=6.8 Hz, 1H), 8.14 (s, 1H); MS m/e 279 (MH+).

후처리

  1. extractionextracted with ethyl ether (30 mL×3)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5)

출처 및 근거

ORD 기록
ord-99ab55077d4f4d628237162ea7b5467e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618839

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