Methyl Acrylate → 3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester

HRID 1665905노트

반응식

HRID 1665905 반응식
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6](OS(C(F)(F)F)(=O)=O)=[C:5]([CH3:18])[CH:4]=1)=[O:2].C(N(CC)CC)C.[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>CN(C=O)C.C(OCC)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:31][O:30][C:26](=[O:29])[CH:27]=[CH:28][C:6]1[C:7]([CH3:9])=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][C:5]=1[CH3:18]

참가 물질

8

반응물 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 544771104-Formyl-2,6-dimethylphenyl trifluoromethanesulfonate

생성물 1

HCID 765393073-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester수율 79.6%

시약·촉매·용매 4

HCID 812191,3-Bis(diphenylphosphino)propane촉매HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
115 °C

실험 절차

To a stirred solution of trifluoro-methanesulfonic acid 4-formyl-2,6-dimethyl-phenyl ester (4.7 g, 16.7 mmol) in dry DMF (75 mL) under argon is sequentially added at rt triethylamine (3.4 g, 33.3 mmol), methyl acrylate (14.3 g, 167 mmol), 1,3-bis-(diphenylphosphino)-propane (378 mg, 0.92 mmol) and Pd(OAc)2 (187 mg, 0.83 mmol). The mixture is heated to 115° C. and stirred for 5 h. The mixture is diluted with diethyl ether (350 mL) and washed twice with aq. 1 N HCl and once with sat. aq. NaHCO3. The organic extract is dried over MgSO4, filtered and evaporated. The residue is purified by CC on silica gel eluting with heptane:EA 5:1 to give 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester (2.9 g) as a slightly yellow solid; LC-MS: tR=0.96 min.

후처리

  1. washwashed twice with aq. 1 N HCl and once with sat. aq. NaHCO3
  2. extractionThe organic extract
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by CC on silica gel eluting with heptane:EA 5:1

출처 및 근거

ORD 기록
ord-62028ba17af4459d848031701abf3eac
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039644B2

반응 노트

불러오는 중…