Sodium Bicarbonate → 2-tert-Butyl-5-methyl-oxazole-4-carboxylic acid methyl ester

HRID 1897559ノート

反応式

HRID 1897559 の反応式
O=[C:2]([CH3:15])[CH:3]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[C:4]([O:6][CH3:7])=[O:5].C([O-])(O)=O.[Na+]>P(Cl)(Cl)(Cl)=O>[C:10]([C:9]1[O:14][C:2]([CH3:15])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[N:8]=1)([CH3:13])([CH3:12])[CH3:11]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 57659743Methyl 3-oxo-2-(pivalamido)butanoate

生成物 1

HCID 576597452-tert-Butyl-5-methyl-oxazole-4-carboxylic acid methyl ester収率 22.3%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

A solution of methyl 3-oxo-2-(pivalamido)butanoate (0.22 g, 1.0 mmol) in phosphorus oxychloride (1.5 mL) was heated at 110° C. for 30 min. The reaction was cooled in an ice bath, and saturated aqueous NaHCO3 was slowly added until the mixture was basic. The reaction was extracted with CH2Cl2, and the extracts were washed with saturated aqueous NaHCO3 and water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (0%-40% EtOAc-hexanes) to obtain methyl 2-tert-butyl-5-methyloxazole-4-carboxylate (44 mg, 22% yield). 1H NMR (400 MHz, CDCl3) δ 3.90 (s, 3H, 2.60 (s, 3H), 1.39 (s, 9H) ppm. LC/MS: m/z 198.3 (M+H)+ at 2.83 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

後処理

  1. temperatureThe reaction was cooled in an ice bath
  2. extractionThe reaction was extracted with CH2Cl2
  3. washthe extracts were washed with saturated aqueous NaHCO3 and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography (0%-40% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-7b5e08e9715344e1963db9e7ce28e2d1
出典データセット
uspto-grants-2013_08
特許番号
US08519137B2

反応ノート

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