HCID 68182046, 화합물 → 2-{5-[(Oxan-2-yloxy)methyl]-1,2-oxazol-3-yl}but-3-yn-2-ol

HRID 1398594노트

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HRID 1398594 반응식
[C:1]([Mg]Br)#[CH:2].[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18](=[O:20])[CH3:19])[CH:14]=1>C1COCC1>[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18]([OH:20])([C:1]#[CH:2])[CH3:19])[CH:14]=1

참가 물질

4

반응물 2

HCID 68182046HCID 68182046, 화합물HCID 178418486HCID 178418486, 화합물

생성물 1

HCID 866695982-{5-[(Oxan-2-yloxy)methyl]-1,2-oxazol-3-yl}but-3-yn-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethynylmagnesium bromide (2.93 mL of a0.5M solution in THF, 1.47 mmol) at 0° C. was slowly added 1-{5-[(oxan-2-yloxy)methyl]-1,2-oxazol-3-yl}ethanone (220 mg, 0.98 mmol) in THF (5 mL). The reaction mixture was allowed to warm to RT and stirred for 45 minutes. The reaction mixture was quenched with aqueous saturated NH4Cl solution (10 mL) and the organics were removed in vacuo. The product was extracted into EtOAc (20 ml×2) and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Isolute column, 10-30% EtOAc in heptanes) to give the title product as a pale yellow oil: 1H NMR (250 MHz, CDCl3) delta 1.93-1.40 (9H, m), 2.66 (1H, s), 2.85 (1H, s), 3.69-3.46 (1H, m), 3.93-3.79 (1H, m), 4.94-4.54 (3H, m), 6.38 (1H, s); LC-MS: m/z=+251.95 (M+H)+.

후처리

  1. customat 0° C.
  2. customThe reaction mixture was quenched with aqueous saturated NH4Cl solution (10 mL)
  3. customthe organics were removed in vacuo
  4. extractionThe product was extracted into EtOAc (20 ml×2)
  5. dry with materialthe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (Isolute column, 10-30% EtOAc in heptanes)

출처 및 근거

ORD 기록
ord-f3c89c9613f648ad923371d743857e3a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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