Propargyl alcohol → HCID 14457169, compound

HRID 1085203Notes

Reaction equation

HRID 1085203 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[O:13]=[C:14]1[NH:18][C:17]([C:19]([F:22])([F:21])[F:20])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:15]1.[C:28]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:33]=CC=C[CH:29]=1.C(O)C#C>O.O1CCCC1>[O:13]=[C:14]1[N:18]([CH2:33][C:28]#[CH:29])[C:17]([C:19]([F:20])([F:21])[F:22])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:15]1

Participants

7

Reactant 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13070077Ethyl 2-oxo-4-(trifluoromethyl)-2,3-dihydro-1,3-oxazole-5-carboxylate

Product 1

HCID 14457169HCID 14457169, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

5.4 ml of diethyl azodicarboxylate were added at 10 C to a solution of 7 g of ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-oxazol-5-carboxylate [prepared as in Patent No. EP 027,020], 70 ml of tetrahydrofuran, 8.15 g of triphenylphosphine and 3.3 ml of propargyl alcohol and the mixture was stirred for one hour at 20° C. The mixture was poured into water and was extracted with ethyl acetate, dried, filtered and concentrated. The residue was chromatographed on silica and eluted with a hexaneethyl acetate mixture (85-15) to obtain 4.6 g of the expected product melting at 72° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica
  6. washeluted with a hexaneethyl acetate mixture (85-15)

Sources & evidence

ORD record
ord-9c4ffb0e00cb4c07a35144202d5cda7e
Source dataset
uspto-grants-1991_04
Patent number
US05008281

Reaction notes

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