1-(5-(Hydroxymethyl)isoxazol-3-yl)ethanone → 2-[5-(Hydroxymethyl)isoxazol-3-yl]but-3-yn-2-ol

HRID 1398540노트

반응식

HRID 1398540 반응식
[C:1]([Mg]Br)#[CH:2].[OH:5][CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12](=[O:14])[CH3:13])[CH:8]=1>C1COCC1>[OH:5][CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]([OH:14])([C:1]#[CH:2])[CH3:13])[CH:8]=1

참가 물질

4

반응물 2

HCID 105587091-(5-(Hydroxymethyl)isoxazol-3-yl)ethanoneHCID 178418486HCID 178418486, 화합물

생성물 1

HCID 866695832-[5-(Hydroxymethyl)isoxazol-3-yl]but-3-yn-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethynylmagnesium bromide (0.5M in THF, 99 mL, 49.0 mmol) at 0° C. under N2 was added a solution of 1-[5-(hydroxymethyl)isoxazol-3-yl]ethanone (prepared according to Synthesis 2005, 20, 3541) (4.10 g, 29.0 mmol) in dry THF (25 mL) over 20 minutes. The reaction mixture was warmed to RT for 1.5 hr, quenched by dropwise addition of saturated aqueous ammonium chloride (20 mL) and concentrated in vacuo. After re-dissolving the residue in EtOAc (100 mL), the aqueous phase was removed, diluted with water to dissolve all suspended solids and washed with EtOAc (100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to furnish the crude title compound as a red-brown syrup: 1H NMR (500 MHz, CDCl3) delta 1.88 (3H, s), 2.67 (1H, s), 4.77 (2H, s), 6.39 (1H, s); LC-MS: m/z=+167.9 (M+H)+. This compound, with LC-MS purity=88% UV, was used in the next step without further purification.

후처리

  1. customquenched by dropwise addition of saturated aqueous ammonium chloride (20 mL)
  2. concentrationconcentrated in vacuo
  3. dissolutionAfter re-dissolving the residue in EtOAc (100 mL)
  4. customthe aqueous phase was removed
  5. additiondiluted with water
  6. dissolutionto dissolve all suspended solids
  7. washwashed with EtOAc (100 mL)
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-41212ee8c6da47af9d57de6c7508aade
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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