N-methyl-2-pyrrolidone → HCID 21706189, compound

HRID 848416Notes

Reaction equation

HRID 848416 reaction equation
[CH3:1][O:2][C:3]1[C:4]#[C:5][CH:6]=[CH:7][CH:8]=1.[CH3:9][N:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:12]2[CH2:13][CH2:14][N:10]([CH3:9])[C:11]2=[O:15])[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 178489254HCID 178489254, compound

Product 1

HCID 21706189HCID 21706189, compound

Procedure

Following the procedure of Example 3, reaction of the lithium anion of 1-methyl-2-pyrrolidone with m-methoxybenzyne (from lithium 2,2,6,6-tetramethylpiperidide and o-chloroanisole) followed by aqueous workup gives 3-(3-methoxyphenyl)-1-methyl-2-pyrrolidone. Removal of the protecting group using iodotrimethylsilane gives the title compound m.p. 113°-4° C. (ethylacetate-hexane).

Sources & evidence

ORD record
ord-5cefe3a0446d42a4a30a476f96d28a85
Source dataset
uspto-grants-1981_10
Patent number
US04296029

Reaction notes

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