Water → HCID 20214969, compound

HRID 1905714Notes

Reaction equation

HRID 1905714 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.C1(C)C=CC(S([Cl:29])(=O)=O)=CC=1.O>O1CCCC1>[Cl:29][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 12548376HCID 12548376, compoundHCID 178418339Butyllithium

Product 1

HCID 20214969HCID 20214969, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-(3-fluorophenyl)-4,4-dimethyloxazoline (36.7 g) in dry tetrahydrofuran (500 ml.) at -65° C. was added dropwise n-butyl-lithium (119 ml. of 1.6M solution in hexane). The solution was stirred at the same temperature for 1 hour and then a solution of 4-toluenesulphonic chloride (36.2 g.) in dry tetrahydrofuran (250 ml.) was added over 45 minutes, maintaining the temperature below -50° C. The mixture was stirred at -50° C. for 1 hour and then allowed to warm up to room temperature and stirred for a further 2 hours. An excess of water was added and the mixture was evaporated to a low volume and extracted several times with diethyl ether. The combined extracts were washed with diluted sodium hydroxide solution, water and then dried over sodium sulphate. Evaporation of the solvent gave an oil which was distilled to give 2-(2-chloro-3-fluorophenyl)-4,4-dimethyloxazoline (29.0 g.), b.p. 138°-140° C. at 15 m.m. Found: C, 57.93; H, 4.77; N, 6.20. C11H11ClFNO requires: C, 58.03; H, 4.87; N, 6.15%.

Workup

  1. temperaturemaintaining the temperature below -50° C
  2. stirringThe mixture was stirred at -50° C. for 1 hour
  3. stirringstirred for a further 2 hours
  4. customthe mixture was evaporated to a low volume
  5. extractionextracted several times with diethyl ether
  6. washThe combined extracts were washed with diluted sodium hydroxide solution, water
  7. dry with materialdried over sodium sulphate
  8. customEvaporation of the solvent
  9. customgave an oil which
  10. distillationwas distilled

Sources & evidence

ORD record
ord-a647d10e153843ea9666d97dc07dc305
Source dataset
uspto-grants-1987_03
Patent number
US04647565

Reaction notes

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