L-Serine → HCID 67033549, compound

HRID 539106Notes

Reaction equation

HRID 539106 reaction equation
[H-].[Na+].I[CH2:4][CH3:5].[C:6]1([C:12]2[O:13][CH2:14][C@H:15]([CH2:17][OH:18])[N:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N[C@H](C(O)=O)CO>C1COCC1.O>[CH2:4]([O:18][CH2:17][C@H:15]1[CH2:14][O:13][C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[N:16]1)[CH3:5]

Participants

7

Reactant 4

HCID 5951L-SerineHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13686102HCID 13686102, compound

Product 1

HCID 67033549HCID 67033549, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of sodium hydride (354 mg, 8.86 mmol) and iodoethane (0.90 ml, 11.2 mmol) in anhydrous THF (22 mL) was chilled to 0° C. A solution of (S)-(2-phenyl-4,5-dihydrooxazol-4-yl)methanol (785 mg, 4.43 mmol) (Synthesis, 1993, 2, 250-262; using D-, instead of L-serine as a starting material) in 10 ml anhydrous THF was then added dropwise to the reaction mixture. The resulting mixture was allowed to warm to ambient temperature, and stirred overnight. After addition of water, the mixture was extracted with EtOAc. The combined organic extracts were dried and concentrated to afford (S)-4-(ethoxymethyl)-2-phenyl-4,5-dihydrooxazole as a clear, light-brown oil (0.981 g, 108%), which was used directly in the next step.

Workup

  1. temperatureto warm to ambient temperature
  2. extractionthe mixture was extracted with EtOAc
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b7d310063ece408fad5f66bde125dbe7
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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