Tetrahydrofuran → HCID 13093546, compound

HRID 434852Notes

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-7f386d77482140d79f3e8eb3b20dd214
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04399296

Reaction notes

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