Tetrahydrofuran → Ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[CH2:25]1COCC1>>[O:14]=[C:13]1[NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH2:9][CH3:25])=[O:7])=[CH:4][C:3]=2[O:12]1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 682631,1'-Carbonyldiimidazole

HCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 15422978Ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate

Procedure

Methyl 4-amino-3-hydroxybenzoate (1.23 g, 7.36 mmol) (commercially available from Pfaltz & Bauer Chemicals Catalog (Order Number A22677)) and 1,1′-carbonyldiimidazole (1.19 g, 7.36 mmol) in 20 mL THF were heated by microwave at 100° C. for 10 minutes. The reaction mixture was used directly for next step. LCMS (API-ES) m/z: 194 (M+H+).

Sources & evidence

ORD record: ord-4fb885a549b0401d84650fbea183dcfa
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919504B2

Reaction notes

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