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Water → ethyl (5-isopropyloxy-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

HRID 733245
ノート
印刷プレビュー

反応式

HRID 733245 の反応式
[H-].[Na+].[CH:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[N:11]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:10]2[OH:21])([CH3:5])[CH3:4].[OH2:22]>COCCOC>[CH:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:4][C:3]([O:6][CH2:7][CH3:15])=[O:22])[N:11]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:10]2=[O:21])([CH3:5])[CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 24758Sodium hydrideHCID 220254425-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one

生成物 1

HCID 86591367ethyl (5-isopropyloxy-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
20 °C

実験手順

Ethyl (5-isopropyloxy-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate is prepared as described in Example 2, starting with 0.149 g of 60% sodium hydride in 20 cm3 of 1,2-dimethoxyethane, 1.23 cm3 of triethyl phosphonoacetate and 1.08 g of 5-isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydro-isoindol-1-one. The mixture is refluxed for 5 hours and then cooled to a temperature in the region of 20° C. The reaction mixture is treated with 100 cm3 of water and the mixture is then extracted with 3 times 100 cm3 of diethyl ether. The organic extracts are combined, washed with 100 cm3 of saturated brine, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is purified by chromatography under argon pressure (80 kPa) on a cartridge of silica gel (particle size 32-63 μm), eluting with a mixture of cyclohexane/ethyl acetate (90/10 by volume) and then with a mixture of cyclohexane/ethyl acetate (80/20 by volume). The fractions comprising the expected product are combined and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.42 g of ethyl (5-isopropyloxy-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate is thus obtained in the form of a colorless oil. (Rf=0.57, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

後処理

  1. customEthyl (5-isopropyloxy-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate is prepared
  2. temperatureThe mixture is refluxed for 5 hours
  3. extractionthe mixture is then extracted with 3 times 100 cm3 of diethyl ether
  4. washwashed with 100 cm3 of saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  8. customThe residue is purified by chromatography under argon pressure (80 kPa) on a cartridge of silica gel (particle size 32-63 μm)
  9. washeluting with a mixture of cyclohexane/ethyl acetate (90/10 by volume)
  10. additionwith a mixture of cyclohexane/ethyl acetate (80/20 by volume)
  11. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

出典と根拠

ORDレコード
ord-c11cbc24914d4814a73d2d0806b277d0
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07589117B2

反応ノート

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