Sodium Chloride → Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

HRID 2261340Notes

Reaction equation

HRID 2261340 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].Cl/[C:6](=[N:12]/[OH:13])/[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[Cl-].[Na+]>O1CCCC1>[OH:4][CH2:1][C:2]1[O:13][N:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylateYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

24.03 g of 2-propene-1-ol and 16.24 g of ethyl (2E)-chloro(hydroxyimino)acetate were dissolved in 100 ml of tetrahydrofuran, and 12.12 ml of triethylamine dissolved in 50 ml of tetrahydrofuran was then added dropwise at 0° C. over 30 minutes. The mixture was stirred at room temperature overnight. After aqueous saturated sodium chloride was added, the reaction mixture was separated into layers. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried over aqueous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 14.22 g of ethyl 5-(hydroxymethyl)-isoxazole-3-carboxylate.

Workup

  1. additionwas then added dropwise at 0° C. over 30 minutes
  2. customthe reaction mixture was separated into layers
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over aqueous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c16b3aff6fd42388e27b73566bfa4be
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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