Chlorotrimethylsilane → HCID 59633969、化合物

HRID 1615062ノート

反応式

HRID 1615062 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].[CH2:24]([C:26]1[CH:42]=[CH:41][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35](I)=[CH:34][C:33]=2[O:39][CH3:40])=[CH:28][CH:27]=1)[CH3:25].[NH4+].[Cl-]>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]>[CH2:24]([C:26]1[CH:42]=[CH:41][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([CH:21]3[CH2:22][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20]3)=[CH:34][C:33]=2[O:39][CH3:40])=[CH:28][CH:27]=1)[CH3:25]

参加物

10

反応物 6

HCID 6397ChlorotrimethylsilaneHCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 59633913HCID 59633913、化合物2 回

生成物 1

HCID 59633969HCID 59633969、化合物収率 52%

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 (20.7 g) and lithium chloride (10 g) in THF (120 mL) were added dibromoethane (2 mL) and chlorotrimethylsilane (3 mL) at 70° C. under argon atmosphere. The mixture was stirred at 70° C. for 10 min. A solution of 1-Boc-3-iodoazetidine (67 g) in THF (120 mL) was added dropwise to the mixture at RT. The reaction mixture was stirred for 1 hr. To the mixture were added a solution of 1-(4-ethylbenzyloxy)-4-iodo-2-methoxybenzene (58.1 g) prepared in (1) in THF (120 mL) and bis(triphenylphosphine)palladium (II) dichloride (0.49 g). The reaction mixture was stirred at RT for 3 hr. Saturated aqueous NH4Cl was added to the reaction mixture and the mixture was 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=4/1) to give the title compound (32.4 g, 52%).

後処理

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

出典と根拠

ORDレコード
ord-9dc5629361fd43a19e84ffbb900a68c0
出典データセット
uspto-grants-2014_07
特許番号
US08765739B2

反応ノート

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