Isobutylene oxide → Methyl 5-(2-hydroxy-2-methylpropoxy)-2-nitrobenzoate

HRID 467794

反応式

HRID 467794 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:15][C:16]1([CH3:19])[CH2:18][O:17]1.C(=O)([O-])[O-].[K+].[K+].O.P([O-])(O)(O)=O.[Na+]>C(#N)C.O>[OH:17][C:16]([CH3:19])([CH3:18])[CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

7

反応物 4

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

生成物 1

HCID 70099919Methyl 5-(2-hydroxy-2-methylpropoxy)-2-nitrobenzoate収率 29.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

A mixture of methyl 5-hydroxy-2-nitrobenzoate (0.5 g, 2.54 mmol), 2,2-dimethyloxirane (6.86 ml, 7.61 mmol), potassium carbonate (351 mg, 2.54 mmol) and sodium dihydrogen phosphate monohydrate (350 mg, 2.54 mmol) in acetonitrile (4 ml) and water (0.6 ml) was stirred at 140° (5 bar) in a steel bomb for 6 hr. After cooling to r.t, the mixture was diluted with water, extracted with AcOEt, dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography using a methylenechloride/MeOH gradient to obtain the title compound (200 mg, 29%) as light yellow viscous oil.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with AcOEt
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-10d865e4ee694388b6ecaffefeee391d
出典データセット
uspto-grants-2014_01
特許番号
US08623866B2

関連ノート

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