Add time:08/19/2019 Source:sciencedirect.com
7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one 2 was converted into 3-(2′-tert-butyldimethylsilyloxy-4′-methoxyphenyl)-N-methyl-N-phenylpropanamide 25 and reaction of this with methyl trifluoromethanesulfonate, followed by reaction with sodium methoxide, gave 2,2,7-trimethoxy-2H-1-benzopyran1a in 55% overall yield from 25. A similar methylation/methoxide sequence using 3-(2′-benzyloxy-4′-methoxyphenyl)-N-methyl-N-phenylpropanamide 18 gave a mixture which contained trimethyl 3-(2′-benzyloxy-4′-methoxyphenyl)orthopropanoate 20a and reaction of this mixture with a solution of sodium in tert-butanol gave a product in which 2,2,7-trimethoxy-2H-1-benzopyran1a was detected, but not isolable.
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