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

HRID 467794

반응식

HRID 467794 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-10d865e4ee694388b6ecaffefeee391d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623866B2

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