3,3-Dimethylbutanoyl chloride → HCID 68709936, compound

Participants

Reaction Steps

Using 3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-1-benzofuran obtained in Reference Example 347, a mixture of cis isomer and trans isomer (3:2) of 3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran was synthesized in the same manner as in Reference Example 199. Using the mixture as it is as the compound, a mixture of cis isomer and trans isomer of 5-bromo-3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran was obtained in the same manner as in Reference Example 23. Using the compound, a mixture of cis isomer and trans isomer of N-benzyl-(3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)amine was obtained in the same manner as in Reference Example 24. Using the compound, (3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)amine was synthesized in the same manner as in Reference Example 30. Using the compound and tert-butylacetyl chloride, a mixture of cis isomer and trans isomer of N-(3-(4-isopropylphenyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide was obtained in the same manner as in Example 1. The compound was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to synthesize the title compound. Yield: 18%. Melting point: 143-144° C. (hexane)

Provenance & Evidence