Tri-o-tolylphosphine → Methyl 2-acetylamino-3-(4-benzyloxy-3,5-dimethyl-phenyl)-acrylate

HRID 643104ノート

反応式

HRID 643104 の反応式
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([NH:21][C:22](=[CH2:27])[C:23]([O:25][CH3:26])=[O:24])(=[O:20])[CH3:19].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]([NH:21][C:22](=[CH:27][C:12]1[CH:13]=[C:14]([CH3:15])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH3:17])[CH:11]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:20])[CH3:19]

参加物

7

反応物 3

HCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 229631332-(Benzyloxy)-5-bromo-1,3-dimethylbenzene

生成物 1

HCID 67273532Methyl 2-acetylamino-3-(4-benzyloxy-3,5-dimethyl-phenyl)-acrylate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

Under a nitrogen atmosphere a mixture of 40.0 g (137 mmol) 2-benzyloxy-5-bromo-1,3-dimethylbenzene and 24.1 g (165 mmol) methyl 2-acetylamino-acrylate in 420 mL triethylamine and 200 mL acetonitrile was combined with 3.5 g (11.2 mmol) tri-o-tolyl-phosphane and 2.5 g (11.1 mmol) Pd(OAc)2 and stirred for 18 h at 80° C. The precipitate was suction filtered, the filtrate was evaporated down i.vac. and combined with 800 mL DCM and 800 mL water. The organic phase was separated off, suction filtered through Na2SO4, the solvent was eliminated i.vac., the residue was stirred with EtOAc, suction filtered and dried i.vac.

後処理

  1. filtrationfiltered
  2. customthe filtrate was evaporated down i.vac
  3. customThe organic phase was separated off
  4. filtrationsuction filtered through Na2SO4
  5. stirring, the residue was stirred with EtOAc, suction
  6. filtrationfiltered
  7. customdried i.vac

出典と根拠

ORDレコード
ord-6d35d503ee0f4e7da2b75a700a59081d
出典データセット
uspto-grants-2010_04
特許番号
US07696209B2

反応ノート

読み込み中…