1,3-Oxazole-2-carboxaldehyde → Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

HRID 2375740Notes

Reaction equation

HRID 2375740 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.[O:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]=[O:22]>C1COCC1>[O:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:9][CH:10]=1)[OH:22]

Participants

4

Reactant 2

HCID 147866091,3-Oxazole-2-carboxaldehydeHCID 178419637HCID 178419637, compound

Product 1

HCID 59855140Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanolYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Tetrahydro-3H-pyranoxy)phenylmagnesium bromide (0.5 M in THF, 6.7 mmol) was added dropwise to a solution of oxazole-2-carbaldehyde (5.15 mmol) in THF (8 mL). After stirring at room temperature for 2.5 hours, the reaction was quenched with water, extracted with EtOAc (200 mL), the organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (silica gel, 1:2 EtOAc/hexane) to obtain compound 10.1 (3.1 mmol). MS ESI (pos.) m/e:276(M+H). 1H NMR (400 MHz) (DMSO-d6) δ 8.02 (s, 1H); 7.31 (d, J=8.7 Hz, 2H); 7.14 (s, 1H); 6.97-7.01 (m, 2H); 6.27 (d, J=5 Hz, 1H); 5.74 (d, J=5 Hz, 1H); 5.44 (s, 1H); 3.74 (m, 1H); 3.52 (M, 1h); 1.72-1.81 (m, 3H); 1.52-1.60(m, 4H).

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with EtOAc (200 mL)
  3. washthe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel, 1:2 EtOAc/hexane)

Sources & evidence

ORD record
ord-10b447f54f3f4b32befbc2fc8d9ed8b8
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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