Tetrahydrofuran → Oxazol-5-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

HRID 731200Notes

Reaction equation

HRID 731200 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]=[C:19](C=O)[N:18]=[CH:17]1.C1C[O:26][CH2:25]C1>>[O:16]1[C:20]([CH:25]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:9][CH:10]=2)[OH:26])=[CH:19][N:18]=[CH:17]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 142814324-OxazolecarboxaldehydeHCID 178419637HCID 178419637, compound

Product 1

HCID 57835730Oxazol-5-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

Conditions

Temperature
-78 °C

Procedure

4-(2-Tetrahydro-3H-pyranoxy)phenylmagnesium bromide (120 mL, 0.5 M in THF, 60 mmol) was added dropwise to a solution of oxazole-4-carbaldehyde (4.85 g, 50 mmol) in THF (90 mL) at −78° C. After stirring at −78° C. for 21 hours, the reaction was quenched with saturated NH4Cl (aq) and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), the organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 17 g of the crude product 75.1, which was used in the next reaction without further purification.

Workup

  1. customthe reaction was quenched with saturated NH4Cl (aq)
  2. temperaturewarmed to room temperature
  3. extractionThe mixture was extracted with EtOAc (500 mL)
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2e9f57fb9bf4d41a6199a4943f9a498
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

Loading…