Triethylamine → 3-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester

HRID 383016

반응식

HRID 383016 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6](I)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH:41]([Si:43]([CH3:46])([CH3:45])[CH3:44])=[CH2:42]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2].[N+]([O-])([O-])=O.[Ag+]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([CH:42]=[CH:41][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 79102VinyltrimethylsilaneHCID 7020599Methyl 3-iodo-5-nitrobenzoate

생성물 1

HCID 543670333-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester

시약·촉매·용매 3

HCID 24470Silver Nitrate촉매HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of 3-iodo-5-nitrobenzoic acid methyl ester (307 mg, 1.0 mmol), Pd(OAc)2 (67 mg, 0.30 mmol), triphenylphosphine (0.032 g, 0.60 mmol), AgNO3 (170 mg, 1.0 mmol), triethylamine (0.167 ml, 1.2 mmol) and vinyltrimethylsilane (0.309 ml, 2.0 mmol) was dissolved in acetonitrile (10 ml) and the solution was heated to 60° C. in a closed vessel for 48 h. The precipitated salts were filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel using a mixture of ethyl acetate and heptane (1:11) as the eluent. Yield: 210 mg (75%).

후처리

  1. filtrationThe precipitated salts were filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel using
  4. additiona mixture of ethyl acetate and heptane (1:11) as the eluent

출처 및 근거

ORD 기록
ord-50cc083063be40b48dc71ffea5d405d1
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310243B1

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