1-(Chloromethyl)-4-iodobenzene → Ethyl 18-(p-iodophenyl)octadecanoate
反応式
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>CC(N(C)C)=O.[Zn].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].IC1C=CC(CCCCCCCCCCCCCCCCCCO)=CC=1>[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:26][CH:25]=1参加物
実験手順
Zinc powder (70 mg, 1.06 mmol) was dried at 70° C. for 30 min in a sealed tube, then DMA (0.4 ml) and solid 12 (9 mg, 0.04 mmol) were added. After stirring for 10 min, a solution of ethyl 17-iodo-heptadecanoate 80 (300 mg, 0.71 mmol) in DMA (1.5 ml) was added and the reaction mixture was stirred in the sealed tube for 11 h at 70° C. In a 10-ml flask, Ni(COD)2 (10 mg, 0.04 mmol), (R)-(s-Bu)-Pybox (or (S)-(s-Bu)-Pybox) (23 mg, 0.07 mmol) and p-iodobenzyl chloride 82 (252 mg, 1 mmol) were dissolved in DMA (1.5 ml), then organozinc solution 81 was added via cannula. The mixture was stirred at room temperature for 15 h, and the reaction was quenched by addition of aqueous NH4Cl, extracted with EtOAc, the extract was dried over Na2SO4 and evaporated. Chromatography of the crude product in hexane-ether (97:3) yielded the compound 37 (276 mg, 76%).
後処理
- stirringthe reaction mixture was stirred in the sealed tube for 11 h at 70° C
- stirringThe mixture was stirred at room temperature for 15 h
- customthe reaction was quenched by addition of aqueous NH4Cl
- extractionextracted with EtOAc
- dry with materialthe extract was dried over Na2SO4
- customevaporated
出典と根拠
- ORDレコード
- ord-c3c51c7e1e64448e9c1e26e6e91eb2b3
- 出典データセット
- uspto-grants-2011_02
- 特許番号
- US07893286B2
反応ノート
読み込み中…