Water → HCID 12527052, compound

HRID 1461760Notes

Reaction equation

HRID 1461760 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.C([Li])(CC)C.CN(C)[CH:22]=[O:23].O>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[C:6]([CH:22]=[O:23])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6399892-(4-chlorophenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazoleHCID 178418400CID 53628100

Product 1

HCID 12527052HCID 12527052, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 16 g (76 mM) of 2-(4-chlorophenyl)-4,4-dimethyl-4,5-dihydrooxazole in 60 ml of dry tetrahydrofuran at -78° C. under an inert atmosphere was added dropwise 75 ml of 1.4M sec-butyllithium in hexane. After 1 hour 9.7 ml of freshly distilled dimethylformamide in 20 ml of tetrahydrofuran was added and stirring was continued for 2 hours at room temperature. The mixture was poured into water (200 ml) and extracted with diethylether (2×100 ml), dried and evaporated to yield the crude product. Vacuum distillation, bp 140-1500° C./0.4 mm gave the title compound as a pale yellow oil.

Workup

  1. extractionextracted with diethylether (2×100 ml)
  2. customdried
  3. customevaporated
  4. customto yield the crude product
  5. distillationVacuum distillation, bp 140-1500° C./0.4 mm

Sources & evidence

ORD record
ord-c6f2c8709a5c4b72a7e51ceb61b3dd38
Source dataset
uspto-grants-1991_12
Patent number
US05077299

Reaction notes

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