Hydrochloric Acid → HCID 59659179, compound

HRID 858197Notes

Reaction equation

HRID 858197 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][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H: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][C@@H:17]1[CH2:18][CH2:19][CH2:20][C@H: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 59094684cis-3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexanol

Product 1

HCID 59659179HCID 59659179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of cis-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 hydrochloric acid 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-(cis-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-f32b898f0a5e4359b91727f42fa4b82a
Source dataset
uspto-grants-2006_12
Patent number
US07148246B2

Reaction notes

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