Water → Ethyl 5-butoxy-1,3-oxazole-2-carboxylate

HRID 17987ノート

反応式

HRID 17987 の反応式
[CH2:1]([O:3][C:4](=[O:16])[C:5]([NH:7][CH2:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=O)[CH3:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>C(#N)C>[CH2:12]([O:11][C:9]1[O:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:16])=[N:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

参加物

5

反応物 3

HCID 962WaterHCID 14812Phosphorus oxide (P4O10)HCID 69643286butyl N-[ethoxy(oxo)acetyl]glycinate

生成物 1

HCID 66996945Ethyl 5-butoxy-1,3-oxazole-2-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a solution of butyl N-[ethoxy(oxo)acetyl]glycinate (783 g, 3.38 mol) in acetonitrile (8 L) in a 50 L glass reactor with overhead stirrer, phosphorus pentoxide (415 g, 2.92 mol) was added in portions. The reaction was heated at 60° C. for 1 hour. The product mixture was cooled, and water (8 L) was added with the mixture maintained at 20° C. The resultant mixture was extracted with dichloromethane (8 L, and 3 times 2 L). The organic extracts were combined, washed twice with saturated aqueous sodium bicarbonate (8 L total), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residual oil was subjected to column chromatography on silica gel eluting with 0-30% heptane/ethyl acetate gradient. Collection and concentration of appropriate fractions provided the title material.

後処理

  1. temperatureThe product mixture was cooled
  2. temperaturemaintained at 20° C
  3. extractionThe resultant mixture was extracted with dichloromethane (8 L, and 3 times 2 L)
  4. washwashed twice with saturated aqueous sodium bicarbonate (8 L total)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

出典と根拠

ORDレコード
ord-5b677e9021ef49aa8905e2820f0536ce
出典データセット
uspto-grants-2010_06
特許番号
US07741315B2

反応ノート

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