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

HRID 1403862노트

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HRID 1403862 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

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온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6cac91480ac94303b326202d43d13ca1
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912199B2

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