Potassium Carbonate → Methyl 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylate

HRID 534834

反応式

HRID 534834 の反応式
[C:1]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=O.C([O-])([O-])=O.[K+].[K+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N+:36]([CH2:38][C:39]([O:41][CH3:42])=[O:40])#[C-:37]>CN(C=O)C>[C:9]([O:8][C:1](=[O:7])[CH2:2][CH2:3][C:4]1[O:6][CH:37]=[N:36][C:38]=1[C:39]([O:41][CH3:42])=[O:40])([CH3:12])([CH3:11])[CH3:10]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 199401P,P-Diphenylphosphinic azideHCID 547815Methyl isocyanoacetateHCID 22317022Butanedioic acid,1-(1,1-dimethylethyl) ester

生成物 1

HCID 66750859Methyl 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylate収率 84.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To an ice-cooled mixture of mono-tert-butyl succinate (5.0 g, 28.7 mmol) and K2CO3 (15.9 g, 114.8 mmol) in DMF (40 mL) were added diphenylphosphoryl azide (11.06 g, 40.2 mmol) and methyl isocyanoacetate (3.41 g, 34.4 mmol). After being stirred at room temperature for 16 h, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica-gel, 9:1-3:7 hexane/ethyl acetate) to give the title compound (6.20 g) as a brown oil.

後処理

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by flash column chromatography (silica-gel, 9:1-3:7 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-f59a35e893d049e8a056d551c7844101
出典データセット
uspto-grants-2014_10
特許番号
US08853215B2

関連ノート

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