Hydrochloric Acid → 4-(3-Allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyloxazole

HRID 253356Notes

Reaction equation

HRID 253356 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27].Cl>CN(C)C=O>[CH2:27]([O:21][CH:17]1[CH2:18][CH2:19][CH2:20][CH:15]([O:14][CH2:13][C:11]2[N:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:9][C:10]=2[CH3:22])[CH2:16]1)[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 219803063-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy)cyclohexanol

Product 1

HCID 587633724-(3-Allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyloxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of the 3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy)cyclohexanol are dissolved in 15 ml of dimethylformamide, and 0.3 g of sodium hydride is added. After 30 minutes, 2.4 g of allyl bromide are added dropwise. The mixture is stirred at room temperature for 5 hours. 15 ml of 1N HCl are then added to the reaction mixture, and the mixture is washed three times with 15 ml of ethyl acetate. The organic phase is dried over magnesium sulfate and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 2.4 g of 4-(3-allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyloxazole as a yellowish oil. C20H24FNO3 (345.42) MS (ESI): 346 (M+H+)

Workup

  1. washthe mixture is washed three times with 15 ml of ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is then removed under reduced pressure
  4. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-70f79245a8654bb08483f65b51182e6c
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

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