tert-Butyl acrylate → Methyl 1-(4-(3-(tert-butoxy)-3-oxopropoxy)phenyl)cyclopropane-1-carboxylate

HRID 1403862ノート

反応式

HRID 1403862 の反応式
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[C:15]([O:19][C:20](=[O:23])[CH:21]=[CH2:22])([CH3:18])([CH3:17])[CH3:16]>>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:22][CH2:21][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:23])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1)=[O:4]

参加物

3

反応物 2

HCID 15458tert-Butyl acrylateHCID 20770793Methyl 1-(4-hydroxyphenyl)cyclopropane-1-carboxylate

生成物 1

HCID 59129236Methyl 1-(4-(3-(tert-butoxy)-3-oxopropoxy)phenyl)cyclopropane-1-carboxylate収率 54%

反応条件

温度
110 °C

実験手順

To a solution of 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic methyl ester (7.0 g, 3.6 mmol) in acrylic tert-butyl ester (50 mL) was added Na (42 mg, 1.8 mmol) at room temperature. The mixture was heated at 110° C. for 1 h. After cooling to room temperature, the resulting mixture was quenched with water and extracted with EtOAc (100 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to give 1-[4-(2-tert-butoxycarbonyl-ethoxy)-phenyl]-cyclopropanecarboxylic methyl ester (6.3 g, 54%) and unreacted start material (3.0 g). 1H NMR (300 MHz, CDCl3) δ 7.24 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H), 4.20 (t, J=6.6 Hz, 2H), 3.62 (s, 3H), 2.69 (t, J=6.6 Hz, 2H), 1.59-1.56 (m, 2H), 1.47 (s, 9H), 1.17-1.42 (m, 2H).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe resulting mixture was quenched with water
  3. extractionextracted with EtOAc (100 mL×3)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. customevaporated under vacuum
  6. customto give the crude product, which
  7. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1)

出典と根拠

ORDレコード
ord-6cac91480ac94303b326202d43d13ca1
出典データセット
uspto-grants-2014_12
特許番号
US08912199B2

反応ノート

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