Triethylamine → Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate

HRID 1506660노트

반응식

HRID 1506660 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[N+:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])#[C-:19]>C1COCC1>[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[O:14][CH:19]=[N:18][C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 533707Ethyl isocyanoacetate

생성물 1

HCID 2739479Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (20 mL, 144 mmol) was added to a solution of 4-chlorobenzoyl chloride (8.4 g, 48 mmol) in THF (100 mL) at 0° C. Ethyl 2-isocyanoacetate (6.0 g, 53 mmol) was added dropwise and the resulting solution was stirred at room temperature for 1 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica column with ethyl acetate and hexanes as eluents to give the desired compound. MS (m/z) 252.1 [M+H]+.

후처리

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column with ethyl acetate and hexanes as eluents

출처 및 근거

ORD 기록
ord-154d0ca150844c3bb7959b249e4d05d0
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09220710B2

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