Water → HCID 18665566, compound

HRID 2395381Notes

Reaction equation

HRID 2395381 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH2:10][C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C=O)C>[C:13]1([C@H:11]2[CH2:10][O:9][C:8]([C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=3)[O:1][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:12]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18665563HCID 18665563, compound

Product 1

HCID 18665566HCID 18665566, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a vigorously stirred mixture of 4,5-dihydro-2-(3-hydroxyphenyl)-4(S)-phenyloxazole (2.04 g, 8.5 mmol) and potassium carbonate (2.36 g, 17 mmol) in DMF (40 ml) was added dropwise over 5 min. a solution of ethyl bromoacetate (1.71 g, 10.2 mmol) in DMF (5 ml) at ambient temperature. The reaction mixture was stirred for 12 h and then poured into water (100 ml). The mixture was extracted with diethyl ether (3×50 ml), and the combined extracts were washed with brine (50 ml), dried (MgSO4) and concentrated under reduced pressure to afford title compound (2.77 g, quant.) as a pale yellow liquid.

Workup

  1. extractionThe mixture was extracted with diethyl ether (3×50 ml)
  2. washthe combined extracts were washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9843f9c4740c4afbb105f9dc03df07e0
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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