Dimethylformamide → 6-[2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine-3-carbaldehyde

HRID 1857523노트

반응식

HRID 1857523 반응식
I[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[N:6][CH:7]=1.CCCCCC.C([Li])CCC.CN(C)[CH:36]=[O:37]>O1CCCC1>[CH:36]([C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[N:6][CH:7]=1)=[O:37]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 185461685-Iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridineHCID 178418339Butyllithium

생성물 1

HCID 185461516-[2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine-3-carbaldehyde수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (2.5 g) in tetrahydrofuran (40 ml) was added dropwise, at -65° C. under nitrogen streams, a hexane solution of n-butyllithium (1.6M, 4.61 ml). The mixture was stirred for 15 minutes at the same temperature, to which was added dropwise N,N-dimethylformamide (0.71 ml). The cooling bath was removed, then the reaction mixture was stirred for further 30 minutes, to which was added a saturated aqueous solution of ammonium chloride (6 ml). The reaction mixture was poured into water, followed by extraction with ethyl acetate. The ethyl acetate was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure to leave 5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (1.5 g, 79%). Recrystallization from ethyl acetate-hexane gave colorless crystals, m.p.99-100° C.

후처리

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture was stirred for further 30 minutes, to which
  3. additionwas added a saturated aqueous solution of ammonium chloride (6 ml)
  4. additionThe reaction mixture was poured into water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe ethyl acetate was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-72ae769704944f85982ec2153e89470e
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147099

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