Methyl Acrylate → (E)-3-(3-Hydroxymethyl-phenyl)-acrylic acid methyl ester

HRID 15005

반응식

HRID 15005 반응식
C(N(CC)CC)C.I[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][OH:13].[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].[Cl-].[NH4+]>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:22][O:21][C:17](=[O:20])/[CH:18]=[CH:19]/[C:9]1[CH:16]=[CH:15][CH:14]=[C:11]([CH2:12][OH:13])[CH:10]=1

참가 물질

7

반응물 4

HCID 7294Methyl Acrylate2회HCID 8471Triethylamine2회HCID 25517Ammonium ChlorideHCID 423003-Iodobenzyl alcohol

생성물 1

HCID 59794688(E)-3-(3-Hydroxymethyl-phenyl)-acrylic acid methyl ester수율 97%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매2회HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

The procedure described in Reich, S. H. etal. J. Med. Chem. 2000, 43, 1670 was followed. Pd(OAc)2 (8.2 mg, 0.037 mmol) and triethylamine (0.360 mL, 2.58 mmol) were added to a solution of 3-iodobenzyl alcohol 15 (0.27 mL, 2.13 mmol) and methyl acrylate 16 (0.220 mL, 2.44 mmol) in CH3CN (4.5 mL). The reaction vessel was sealed with a Teflon screw-cap and was heated at 100° C. for 5 h. At this time, the reaction was allowed to cool to room temperature and the tube was charged with 0.22 mL more of methyl acrylate, 11.7 mg Pd(OAc)2 and 0.360 mL triethylamine. The reaction was heated at 100° C. overnight and then 10 mL saturated ammonium chloride solution was added. The resulting mixture was extracted with dichloromethane (3×40 mL) and the combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (30% ethyl acetate/hexanes) gave 395 mg (97%) of compound 17.

후처리

  1. customscrew-cap
  2. temperatureto cool to room temperature
  3. temperatureThe reaction was heated at 100° C. overnight
  4. extractionThe resulting mixture was extracted with dichloromethane (3×40 mL)
  5. dry with materialthe combined dichloromethane solution was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography on silica gel (30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-a51aab874b354bb2a3c422fc2effc228
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732443B2

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