7-(chloromethyl)-2,2-dimethyl-3H-1-benzofuran

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g of 2,3-dihydro-2,2-dimethyl-7-benzofuranylmethyl chloride and 3.0 g of 1-(4-hydroxyphenyl)-3,3-dimethylurea were dissolved into 20 ml of dried N,N-dimethylformamide, and 2.5 g of anhydrous potassium carbonate was added thereto. After the mixture was stirred at 80° C. for 4 hours, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/1) as a developer to obtain 4.0 g of Compound No. 7 shown in Table 1. was added extracted with ethyl acetate After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g of 2,3-dihydro-2,2-dimethyl-7-benzofuranylmethyl chloride and 3.0 g of 1-(4-hydroxyphenyl)-3,3-dimethylurea were dissolved into 20 ml of dried N,N-dimethylformamide, and 2.5 g of anhydrous potassium carbonate was added thereto. After the mixture was stirred at 80° C. for 4 hours, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/1) as a developer to obtain 4.0 g of Compound No. 7 shown in Table 1. was added extracted with ethyl acetate After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethanol (6.3 grams, 0.035 mole) and concentrated hydrochloric acid (38%) was stirred at ambient temperature for 0.75 hour. The reaction mixture was diluted with water (50 ml) and extracted with diethyl ether. The extract was washed successively with a 10% aqueous solution of sodium hydroxide and a saturated aqueous sodium chloride solution. The dried (sodium sulfate) extract was concentrated under reduced pressure, yielding 7-chloromethyl-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum was consistent with the proposed structure. extracted with diethyl ether The extract was washed successively with a 10% aqueous solution of sodium hydroxide The dried (sodium sulfate) extract was concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g of 2,3-dihydro-2,2-dimethyl-7-benzofuranylmethyl chloride and 3.0 g of 1-(4-hydroxyphenyl)-3,3-dimethylurea were dissolved into 20 ml of dried N,N-dimethylformamide, and 2.5 g of anhydrous potassium carbonate was added thereto. After the mixture was stirred at 80° C. for 4 hours, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/1) as a developer to obtain 4.0 g of Compound No. 7 shown in Table 1. was added extracted with ethyl acetate After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate and ethyl acetate was distilled off