ethyl N,N-dimethylcarbamate

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

Procedure: At 170° C. and 100 mm Hg, 14 g of alpha-naphthol and 18 g of dimethyl urethane were reacted in the presence of 1.5 g of titanium tetra-isopropylate. In 5 hours a 32% convertion of naphthol was obtained, with total selectivity to methyl naphthyl urethane.

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

Procedure: At 150° C. and 100 mm Hg, 14 g of beta-naphthol and 9 g of dimethyl urethane were reacted in the presence of 0.7 g ZnCl2. A conversion of 2% of naphthol to methyl naphthyl urethane was obtained.

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

Procedure: At 150° C. and 100 mm Hg, 14 g of beta-naphthol and 9 g of dimethyl urethane were reacted in the presence of 0.7 g ZnCl2. A conversion of 2% of naphthol to methyl naphthyl urethane was obtained.

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

Procedure: At 160° C. and 100 mm Hg, 14 g of alpha-naphthal and 9 g of dimethyl urethane were reacted in presence of 0.7 g of anhydrous AlCl3. The reaction was continued for 6 hours, removing the methanol formed during the reaction. A 28% conversion of naphthal was obtained, with practically complete selectivity to naphthyl-methyl-urethane. removing the methanol formed during the reaction

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

Procedure: At 160° C. and 100 mm Hg, 14 g of alpha-naphthal and 9 g of dimethyl urethane were reacted in presence of 0.7 g of anhydrous AlCl3. The reaction was continued for 6 hours, removing the methanol formed during the reaction. A 28% conversion of naphthal was obtained, with practically complete selectivity to naphthyl-methyl-urethane. removing the methanol formed during the reaction

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.23 g (0.01 mol) of 4-[4-(tert-butyl)phenyl]-2-methylthiophene, 2.97 mL (0.02 mol) of TMEDA in 30 mL of ether was treated with 13 mL (0.02 mol) of 1.6M BuLi in hexane under stirring at −40° C. Then the reaction mixture was allowed to warm up to r.t. and stirred for 3 h. The reaction mixture was cooled −40° C. and treated with 1.17 g (0.01 mol) of ethyl N,N-dimethylcarbamate in 10 mL of ether. Then the reaction mixture was allowed to warm up to r.t. and was stirred overnight. Resulting mixture was treated with 10% aqueous NH4Cl, organic layer was separated, washed with 10% aqueous NH4Cl and then dried over anhydrous Na2SO4. Solvent was evaporated, the residue was washed with methanol. Yield 2.4 g (about 100%) of red oil. to warm up to r.t. stirred for 3 h The reaction mixture was cooled −40° C. to warm up to r.t. was stirred overnight Resulting mixture was separated washed with 10% aqueous NH4Cl dried over anhydrous Na2SO4 Solvent was evaporated the residue was washed with methanol

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.23 g (0.01 mol) of 4-[4-(tert-butyl)phenyl]-2-methylthiophene, 2.97 mL (0.02 mol) of TMEDA in 30 mL of ether was treated with 13 mL (0.02 mol) of 1.6M BuLi in hexane under stirring at −40° C. Then the reaction mixture was allowed to warm up to r.t. and stirred for 3 h. The reaction mixture was cooled −40° C. and treated with 1.17 g (0.01 mol) of ethyl N,N-dimethylcarbamate in 10 mL of ether. Then the reaction mixture was allowed to warm up to r.t. and was stirred overnight. Resulting mixture was treated with 10% aqueous NH4Cl, organic layer was separated, washed with 10% aqueous NH4Cl and then dried over anhydrous Na2SO4. Solvent was evaporated, the residue was washed with methanol. Yield 2.4 g (about 100%) of red oil. to warm up to r.t. stirred for 3 h The reaction mixture was cooled −40° C. to warm up to r.t. was stirred overnight Resulting mixture was separated washed with 10% aqueous NH4Cl dried over anhydrous Na2SO4 Solvent was evaporated the residue was washed with methanol

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.19 g (0.00991 mol) of 1-methyl-3-(4-methylphenyl)-1H-indole and 3.24 mL (0.0218 mol) of TMEDA in 30 mL of ether was treated with 13.6 mL (0.0218 mol) of 1.6M BuLi in hexane under stirring at −40° C. Then the reaction mixture was allowed to warm up to r.t. and stirred for 4 h. The reaction mixture was cooled to −60° C. and treated with 1.16 g (0.00991 mol) ethyl N,N-dimethylcarbamate in 5 mL of ether. Then the reaction mixture was allowed to warm up to r.t. and was stirred overnight. Resulting mixture was treated with 50 mL of 10% aqueous NH4Cl. The violet precipitate was separated, washed twice with water and dried. Yield 1.04 g (42%). to warm up to r.t. stirred for 4 h The reaction mixture was cooled to −60° C. to warm up to r.t. was stirred overnight Resulting mixture The violet precipitate was separated washed twice with water dried

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 12.88 g (0.074 mol) of 2-methyl-4-phenylthiophene, 23.4 mL (0.16 mol) of TMEDA in 200 mL of diethyl ether (ether) was treated with 100 mL (0.16 mol) of 1.6M BuLi in hexane under stirring at −40° C. Then the reaction mixture was allowed to warm up to room temperature (r.t.) and was stirred for 3 h (white precipitate forms). The reaction mixture was cooled to −40° C. and treated with 8.76 g (0.075 mol) of ethyl N,N-dimethylcarbamate in 25 mL of ether. Then the reaction mixture was allowed to warm up to r.t. and was stirred overnight. Resulting mixture was treated with 10% aqueous NH4Cl, the organic layer was separated and the organic phase was washed with 10% aqueous solution of NH4Cl and then dried by anhydrous Na2SO4. Solvent was evaporated and the residue was washed with methanol. Yield 6.8 g (46%) of red crystals. to warm up to room temperature (r.t.) was stirred for 3 h (white precipitate forms) The reaction mixture was cooled to −40° C. to warm up to r.t. was stirred overnight Resulting mixture the organic layer was separated the organic phase was washed with 10% aqueous solution of NH4Cl dried by anhydrous Na2SO4 Solvent was evaporated the residue was washed with methanol

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 12.88 g (0.074 mol) of 2-methyl-4-phenylthiophene, 23.4 mL (0.16 mol) of TMEDA in 200 mL of diethyl ether (ether) was treated with 100 mL (0.16 mol) of 1.6M BuLi in hexane under stirring at −40° C. Then the reaction mixture was allowed to warm up to room temperature (r.t.) and was stirred for 3 h (white precipitate forms). The reaction mixture was cooled to −40° C. and treated with 8.76 g (0.075 mol) of ethyl N,N-dimethylcarbamate in 25 mL of ether. Then the reaction mixture was allowed to warm up to r.t. and was stirred overnight. Resulting mixture was treated with 10% aqueous NH4Cl, the organic layer was separated and the organic phase was washed with 10% aqueous solution of NH4Cl and then dried by anhydrous Na2SO4. Solvent was evaporated and the residue was washed with methanol. Yield 6.8 g (46%) of red crystals. to warm up to room temperature (r.t.) was stirred for 3 h (white precipitate forms) The reaction mixture was cooled to −40° C. to warm up to r.t. was stirred overnight Resulting mixture the organic layer was separated the organic phase was washed with 10% aqueous solution of NH4Cl dried by anhydrous Na2SO4 Solvent was evaporated the residue was washed with methanol

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

Procedure: At 170° C. and 100 mm Hg, 14 g of alpha-naphthol and 18 g of dimethyl urethane were reacted in the presence of 1.5 g of titanium tetra-isopropylate. In 5 hours a 32% convertion of naphthol was obtained, with total selectivity to methyl naphthyl urethane.

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

Procedure: At 150° C. and 100 mm Hg, 14 g of beta-naphthol and 9 g of dimethyl urethane were reacted in the presence of 0.7 g ZnCl2. A conversion of 2% of naphthol to methyl naphthyl urethane was obtained.