Tetrahydrofuran → HCID 13093546, compound

HRID 544324Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4]=1[CH:15]([OH:21])[C:16](=[NH:20])[O:17]CC.[O:22]1CCC[CH2:23]1>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4]=1[CH:15]1[O:21][C:23](=[O:22])[NH:17][C:16]1=[O:20]

Participants

Reactant 2

HCID 8028Tetrahydrofuran

HCID 20459901HCID 20459901, compound

Product 1

HCID 13093546HCID 13093546, compound

Procedure

By the procedure of Example 12, Method A, ethyl 1-(2,6-dimethoxy-1-naphthyl)-1-hydroxymethanecarboximidate (3.0 g.) in 125 ml. of tetrahydrofuran converted to the desired product. To isolate, the reaction mixture was quenched by pouring slowly into 200 ml. of crushed ice and extracted with two 100 ml. portions of ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered, evaporated to semi-solids (2.6 g.) and crystallized by trituration with ether, affording 5-(2,6-dimethoxy-1-naphthyl)oxazolidine-2,4-dione (0.43 g.; m.p. 175°-180° C.; m/e 287).

Sources & evidence

ORD record: ord-b5be0ba3b8ef4edeb3a0525e52bb0c5d
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04448971

Reaction notes

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