1,4-Dioxane → HCID 53629169, compound

HRID 1896404Notes

Reaction equation

HRID 1896404 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.Cl.N1CCOCC1.O1CCOCC1.[F:20][C:21]([F:27])([F:26])[CH2:22][CH2:23][CH:24]=[O:25]>C(OC)(C)(C)C.O>[OH:25][CH:24]1[O:6][C:2](=[O:5])[CH:3]=[C:23]1[CH2:22][C:21]([F:27])([F:26])[F:20]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 197884Morpholine, hydrochloride (1:1)HCID 27770834,4,4-TrifluorobutanalHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 53629169HCID 53629169, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Glyoxylic acid monohydrate (2.43 g, 26.4 mmol), morpholine hydrochloride (3.59 g, 29 mmol) and dioxane (10.5 ml) are stirred together at room temperature. Water (14 ml) is added and the reaction mixture is stirred for a few minutes until it becomes homogeneous. 4,4,4-trifluorobutyraldehyde x99 (3.16 g, 25.1 mmol) is added and the mixture is stirred for 1 h at room temperature and under reflux conditions overnight. The mixture is diluted in tert-butylmethylether and washed with water. The aqueous phase is re-extracted with tert-butylmethylether. The organic extracts are combined, dried over magnesium sulphate, filtered and concentrated in vacuo to obtain 5-hydroxy-4-(2,2,2-trifluoroethyl)furan-2(5H)-one x100 as a yellow oil (3.76 g, 81%). The product is used in the next reaction without further purification.

Workup

  1. stirringthe mixture is stirred for 1 h at room temperature and under reflux conditions overnight
  2. washwashed with water
  3. extractionThe aqueous phase is re-extracted with tert-butylmethylether
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fcb1c0d19204569acc8775f44d53345
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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