Dibutyltin oxide → HCID 178497739、化合物

HRID 1927397ノート

反応式

HRID 1927397 の反応式
[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)=[C:7]([Cl:43])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N:48]=[N+:49]=[N-:50])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]3[NH:50][N:49]=[N:48][N:40]=3)=[CH:37][CH:38]=2)[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=2)=[C:7]([Cl:43])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57831384Methyl 4-{(3E)-4-{2-[(4-tert-butyl-2-chlorobenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate

生成物 1

HCID 178497739HCID 178497739、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A solution of 478 mg (0.81 mmol) of methyl 4-{(3E)-4-{2-[(4-tert-butyl-2-chlorobenzyl)oxy]-phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate in 10 ml of toluene is mixed with 1116 mg (9.69 mmol) of trimethylsilyl azide and 351 mg (1.21 mmol) of di-n-butyltin oxide and then heated at 80° C. for 12 h. After cooling to room temperature, the mixture is washed with saturated sodium bicarbonate solution. The organic phase is separated off, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The resulting crude product is purified by chromatography on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:2). 144 mg (0.23 mmol, 28% of theory) of a white foam are obtained.

後処理

  1. temperatureAfter cooling to room temperature
  2. washthe mixture is washed with saturated sodium bicarbonate solution
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated to dryness
  8. customThe resulting crude product is purified by chromatography on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:2)
  9. custom144 mg (0.23 mmol, 28% of theory) of a white foam are obtained

出典と根拠

ORDレコード
ord-21fe4027cded4a4d96428b64f4acb27f
出典データセット
uspto-grants-2012_05
特許番号
US08183271B2

反応ノート

読み込み中…