Phosphorus oxychloride → HCID 18174750, compound

HRID 563110Notes

Reaction equation

HRID 563110 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[O:16][C:15](=O)[NH:14][C:13]=2[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:28])=O>N1C=CC=CC=1>[Cl:28][C:15]1[O:16][C:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([F:1])=[CH:3][CH:4]=2)=[C:13]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:14]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18174735HCID 18174735, compound

Product 1

HCID 18174750HCID 18174750, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of ethyl 4-[5-(4-fluoro-1-naphthyl)-2-oxo-4-oxazolin-4-yl]butanoate (3.09 g), phosphorus oxychloride (6.00 g) and pyridine (0.80 g) was heated to 120-130° C. and stirred for 45 minutes. The reaction mixture was poured into 100 ml of ice water and extracted with ethyl acetate (100 ml×2). The organic layer was washed in sequence with a 10% aqueous solution of sodium hydrogen carbonate (50 ml) and a saturated aqueous solution of sodium chloride (50 ml), and dried over anhydrous magnesium sulfate. The organic layer was concentrated, the residue was subjected to silica gel column chromatography, and ethyl 2-chloro-5-(4-fluoro-1-naphthyl)-4-oxazolebutanoate was obtained as a yellow oil (903 mg, 28%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe organic layer was washed in sequence with a 10% aqueous solution of sodium hydrogen carbonate (50 ml)
  3. dry with materiala saturated aqueous solution of sodium chloride (50 ml), and dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-25e6d5746a63422aaa1be2999ad2cb6f
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

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