Chlorotrimethylsilane → HCID 59633933、化合物

HRID 1615052ノート

反応式

HRID 1615052 の反応式
[Cl-].[Li+].BrC(Br)C.Cl[Si](C)(C)C.[C:12]([N:19]1[CH2:22][CH:21](I)[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH:24]1([C:27]2[CH:43]=[CH:42][C:30]([CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36](I)=[CH:35][C:34]=3[O:40][CH3:41])=[CH:29][CH:28]=2)[CH2:26][CH2:25]1>O1CCCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[CH:24]1([C:27]2[CH:43]=[CH:42][C:30]([CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36]([CH:21]4[CH2:22][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20]4)=[CH:35][C:34]=3[O:40][CH3:41])=[CH:29][CH:28]=2)[CH2:25][CH2:26]1

参加物

9

反応物 5

HCID 6397ChlorotrimethylsilaneHCID 112011,1-DibromoethaneHCID 433294Lithium ChlorideHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 59634051HCID 59634051、化合物2 回

生成物 1

HCID 59633933HCID 59633933、化合物

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒3 回HCID 178419050HCID 178419050、化合物溶媒

反応条件

温度
70 °C

実験手順

To a suspension of zinc (3.0 g) and lithium chloride (1.5 g) in THF (25 mL) were added dibromoethane (0.30 mL) and chlorotrimethylsilane (0.44 mL) at 70° C. under argon atmosphere. The mixture was stirred at 70° C. for 10 min. A solution of 1-Boc-3-iodoazetidine (9.8 g) in THF (10 mL) was added dropwise to the mixture at RT. The mixture was stirred at RT for 1 hr. To the mixture were added a solution of 1-(4-cyclopropylbenzyloxy)-4-iodo-2-methoxybenzene (5.3 g) prepared in (3) in THF (15 mL) and bis(triphenylphosphine)palladium (II) dichloride (0.49 g). The reaction mixture was stirred at RT for 3 hr. The reaction mixture was quenched with saturated aqueous NH4C1 and extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1 to 4/1) to give the title compound.

後処理

  1. stirringThe mixture was stirred at RT for 1 hr
  2. stirringThe reaction mixture was stirred at RT for 3 hr
  3. customThe reaction mixture was quenched with saturated aqueous NH4C1
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1 to 4/1)

出典と根拠

ORDレコード
ord-4264a397a6c64c33ab8867c63fcb3112
出典データセット
uspto-grants-2014_07
特許番号
US08765739B2

反応ノート

読み込み中…