Triphenylphosphine → Methyl 2-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylate

HRID 1795022Notes

Reaction equation

HRID 1795022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][CH:11]([CH2:16][OH:17])[C:12]([O:14][CH3:15])=[O:13])=O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:17][CH2:16][CH:11]([C:12]([O:14][CH3:15])=[O:13])[N:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 22184746Methyl 2-[(4-fluorophenyl)carbonylamino]-3-hydroxypropanoate

Product 1

HCID 22184737Methyl 2-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylateYield 149.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 25 ml tetrahydrofuran was added methyl 2-[(4-fluorophenyl)carbonylamino]-3-hydroxypropanoate (0.750 g, 3 mmol), triphenylphosphine (1.0 g, 4.5 mmol) and diisopropylazodicarboxylate (0.800 g, 4.5 mmol). The reaction was stirred at room temperature under nitrogen until SM was shown to be consumed (TLC, 1:1 Ethyl Acetate:Hexane). The reaction mixture was concentrated under reduced pressure and purified using a Flash 40 Column (1:1 EtOAc:Hexane, 20 psi) to yield 1 g of methyl 2-(4-fluorophenyl)-1,3-oxazoline-4-carboxylate (M+1=224.2).

Workup

  1. customto be consumed (TLC, 1:1 Ethyl Acetate:Hexane)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-cbe1af7a56af4ed992c609ec73216240
Source dataset
uspto-grants-2006_04
Patent number
US07026321B2

Reaction notes

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