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

HRID 1817328노트

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HRID 1817328 반응식
[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(Cl)Cl>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]

참가 물질

6

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 14812Phosphorus oxide (P4O10)HCID 69643286butyl N-[ethoxy(oxo)acetyl]glycinate

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

Butyl N-[ethoxy(oxo)acetyl]glycinate (783 g, 3.38 mol) was dissolved in 8 L of acetonitrile in a 50 L Chemglass reactor with overhead stirrer and P2O5 (415 g, 2.92 mol) was added in large portions, watching for exotherm. The reaction was heated to 60° C. for 1 hour and LCMS showed the reaction done. After cooling, water (8 L) was added at 20° C. and the reaction was transferred to a 50 L flask. Methylene chloride (8 L) was added, the layers split and the aqueous layer was extracted with three 2 L volumes of methylene chloride. The combined organic layers were washed with two 4 L portions of saturated aqueous NaHCO3, then dried with MgSO4 and evaporated to give an oil that was purified on silica eluting with 0-30% EtOAc/heptane to give the product as an oil.

후처리

  1. temperatureAfter cooling
  2. customthe reaction was transferred to a 50 L flask
  3. customthe layers split
  4. extractionthe aqueous layer was extracted with three 2 L volumes of methylene chloride
  5. washThe combined organic layers were washed with two 4 L portions of saturated aqueous NaHCO3
  6. dry with materialdried with MgSO4
  7. customevaporated
  8. customto give an oil that
  9. customwas purified on silica eluting with 0-30% EtOAc/heptane

출처 및 근거

ORD 기록
ord-3fd2f298d6214b4f97c385de6bd94e6d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598264B2

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