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

HRID 1398594Notes

Reaction equation

HRID 1398594 reaction equation
[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

Participants

4

Reactant 2

HCID 68182046HCID 68182046, compoundHCID 178418486HCID 178418486, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-f3c89c9613f648ad923371d743857e3a
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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