Water → 2-(2-Cyclohexyl-6-fluoro-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

HRID 586702Notes

Reaction equation

HRID 586702 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:9][C:10]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20](F)[C:11]=1[C:12]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])=O.O.C(OCC)(=O)C>O1CCCC1>[CH:1]1([C:20]2[CH:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:10]([F:9])[C:11]=2[C:12]2[O:17][CH2:16][C:15]([CH3:19])([CH3:18])[N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 223353682,6-Difluoro-N-(2-hydroxy-1,1-dimethylethyl)-4-methoxybenzamideHCID 178478990HCID 178478990, compound

Product 1

HCID 223353022-(2-Cyclohexyl-6-fluoro-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexylmagnesium chloride (22 mL, 2M in diethyl ether, 44 mmol) was added slowly to an ice-cooled solution of the compound from preparation 2 (9.64 g, 40 mmol) in tetrahydrofuran (100 mL), and the solution then stirred at room temperature for 2 hours. Water (10 mL) was added, the mixture poured into ethyl acetate, and washed with a solution of ethylenediaminetetracetic acid disodium salt (24 g) in water (200 mL), then 1N sodium hydroxide solution (100 mL) and brine. The organic solution was dried (MgSO4) and evaporated under reduced pressure to afford the title compound as a colourless oil, 12.4 g.

Workup

  1. temperaturecooled solution of the compound
  2. washwashed with a solution of ethylenediaminetetracetic acid disodium salt (24 g) in water (200 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-839c0d1e64a54bceba7e168f39c7df80
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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