Triphenylphosphine → Methyl 1-(benzo[d]oxazol-2-yl)cyclopropanecarboxylate

HRID 2241357Notes

Reaction equation

HRID 2241357 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]1)=[O:10].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>C1COCC1>[O:10]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C:11]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68513898Methyl 1-((2-hydroxyphenyl)carbamoyl)cyclopropanecarboxylate

Product 1

HCID 68518116Methyl 1-(benzo[d]oxazol-2-yl)cyclopropanecarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of methyl 1-((2-hydroxyphenyl)carbamoyl)cyclopropanecarboxylate (0.147 g, 0.62 mmol) in 2.5 mL THF at room temperature under nitrogen was added triphenylphosphine (0.361 g, 1.375 mmol) followed by DIAD (0.2663 ml, 1.375 mmol). After 2 hours, the reaction mixture was loaded directly onto a Biotage 40S column in THF and was eluted with 9/1 hexanes/EtOAc to provide the desired product as a yellow oil (132 mg, 97%).

Workup

  1. washwas eluted with 9/1 hexanes/EtOAc

Sources & evidence

ORD record
ord-ee6bd76e89ff4c8390a0cdbb0b2c345d
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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