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

HRID 643104노트

반응식

HRID 643104 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d35d503ee0f4e7da2b75a700a59081d
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696209B2

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