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

HRID 53280

反応式

HRID 53280 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11773Triphenylarsine触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-99ab55077d4f4d628237162ea7b5467e
出典データセット
uspto-grants-1997_04
特許番号
US05618839

関連ノート

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