Hydrochloric Acid → {5-[(Morpholin-4-yl)methyl]-1,2-oxazol-3-yl}methanol

HRID 10174Notes

Reaction equation

HRID 10174 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH:13]=[C:12]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:11][N:10]=1.Cl.C([O-])([O-])=O.[K+].[K+]>CO>[N:15]1([CH2:14][C:12]2[O:11][N:10]=[C:9]([CH2:8][OH:7])[CH:13]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21978752HCID 21978752, compound

Product 1

HCID 21978809{5-[(Morpholin-4-yl)methyl]-1,2-oxazol-3-yl}methanolYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[5-((morpholin-4-yl)methyl)isoxazol-3-yl]methyl 2-tetrahydropyranyl ether (1.0 g) was dissolved in methanol (2 mL) and treated with 1 M HCl (aq. 10 mL). The mixture was stirred at room temperature for 1 h, then basified with K2CO3, and extracted with dichloromethane. The organic layers were dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5) to afford [5-((morpholin-4-yl)methyl)-isoxazol-3-yl]methanol (53%). MH+ 199, Rf 0.24 (CH2Cl2/MeOH/NH4OH 92/7.5/0.5).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5)

Sources & evidence

ORD record
ord-71ad9a67baf44ed6bce3a9333c8c2b29
Source dataset
uspto-grants-2006_08
Patent number
US07094779B2

Reaction notes

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