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

HRID 15005

反応式

HRID 15005 の反応式
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

参加物

7

反応物 4

HCID 7294Methyl Acrylate2 回HCID 8471Triethylamine2 回HCID 25517Ammonium ChlorideHCID 423003-Iodobenzyl alcohol

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a51aab874b354bb2a3c422fc2effc228
出典データセット
uspto-grants-2010_06
特許番号
US07732443B2

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