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

HRID 2246656Notes

Reaction equation

HRID 2246656 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 5.1, 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-75900d514d6a490eb2ac19fd221fe699
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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