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Water → 5-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one

HRID 733246
ノート
印刷プレビュー

反応式

HRID 733246 の反応式
[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2=[CH:11][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=[C:7]2[C:6]1=[O:19])[CH:2]([CH3:4])[CH3:3].O>CO.[BH4-].[K+]>[CH:16]([O:15][C:12]1[CH:11]=[C:8]2[C:7](=[CH:14][CH:13]=1)[C:6](=[O:19])[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH:9]2[OH:10])([CH3:18])[CH3:17]
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 2

HCID 962WaterHCID 22025411N-isobutyl-4-isopropyloxyphthalimide

生成物 1

HCID 220254425-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one収率 92.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 4192641Potassium borohydride溶媒

反応条件

温度
20 °C

実験手順

5-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 1.16 g of N-isobutyl-4-isopropyloxyphthalimide in 20 cm3 of methanol and 0.24 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 17 hours and then cooled to a temperature in the region of 0° C. and 30 cm3 of distilled water are added dropwise. The methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C., and 50 cm3 of water are added. The aqueous phase is extracted 3 times with 70 cm3 of ethyl acetate. The organic extracts are combined, washed with 100 cm3 of saturated sodium chloride solution, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.08 g of 5-isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a viscous colorless oil. (Rf=0.50, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

後処理

  1. custom5-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared
  2. additionare added dropwise
  3. customThe methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C., and 50 cm3 of water
  4. additionare added
  5. extractionThe aqueous phase is extracted 3 times with 70 cm3 of ethyl acetate
  6. washwashed with 100 cm3 of saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. 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-8427d63f9c574142a0cfeecc48bd92b8
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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