(2-methyl-2,3-dihydro-1-benzofuran-5-yl)methanol

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

Procedure: To a solution of 853 mg (4.14 mmole) ethyl 2-methyl-2,3-dihydrobenzofuran-5-carboxylate in 9 ml dry tetrahydrafuran under nitrogen was added 157 mg (4.14 mmole) lithium aluminum hydride in portions and the resulting mixture was stirred at room temperature overnight. The mixture was worked up as described in Preparation A, Part (v), to afford 752 mg of product. The NMR spectrum showed the presence of a band at 4.5 ppm, characteristic of a benzyl alcohol CH2 group. TLC with 1:1 hexane/ethyl ether showed one spot at Rf 0.2 (vanillin spray).

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

Procedure: To a solution of 853 mg (4.14 mmole) ethyl 2-methyl-2,3-dihydrobenzofuran-5-carboxylate in 9 ml dry tetrahydrafuran under nitrogen was added 157 mg (4.14 mmole) lithium aluminum hydride in portions and the resulting mixture was stirred at room temperature overnight. The mixture was worked up as described in Preparation A, Part (v), to afford 752 mg of product. The NMR spectrum showed the presence of a band at 4.5 ppm, characteristic of a benzyl alcohol CH2 group. TLC with 1:1 hexane/ethyl ether showed one spot at Rf 0.2 (vanillin spray).

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

Procedure: To a magnetically stirred solution of 680 mg (4.14 mmole) 5-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 100 ml methylene dichloride was added 5.44 g manganese dioxide in one portion and the mixture stirred at room temperature overnight or until the reaction was complete as evidenced by thin-layer chromatography. The mixture was then filtered and the solvent evaporated to provide the title compound in quantitative yield. 1H-NMR(CDCl3)ppm(delta): 1.6 (d, 3H), 2.7-3.6 (m, 1H), 5.1 (m, 2H), 6.8 (d, 1H), 7.6 (m, 2H), 9.8 (s, 1H). The mixture was then filtered the solvent evaporated

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

Procedure: To a magnetically stirred solution of 680 mg (4.14 mmole) 5-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 100 ml methylene dichloride was added 5.44 g manganese dioxide in one portion and the mixture stirred at room temperature overnight or until the reaction was complete as evidenced by thin-layer chromatography. The mixture was then filtered and the solvent evaporated to provide the title compound in quantitative yield. 1H-NMR(CDCl3)ppm(delta): 1.6 (d, 3H), 2.7-3.6 (m, 1H), 5.1 (m, 2H), 6.8 (d, 1H), 7.6 (m, 2H), 9.8 (s, 1H). The mixture was then filtered the solvent evaporated

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

Procedure: To a solution of 853 mg (4.14 mmole) ethyl 2-methyl-2,3-dihydrobenzofuran-5-carboxylate in 9 ml dry tetrahydrafuran under nitrogen was added 157 mg (4.14 mmole) lithium aluminum hydride in portions and the resulting mixture was stirred at room temperature overnight. The mixture was worked up as described in Preparation A, Part (v), to afford 752 mg of product. The NMR spectrum showed the presence of a band at 4.5 ppm, characteristic of a benzyl alcohol CH2 group. TLC with 1:1 hexane/ethyl ether showed one spot at Rf 0.2 (vanillin spray).

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

Procedure: To a magnetically stirred solution of 680 mg (4.14 mmole) 5-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 100 ml methylene dichloride was added 5.44 g manganese dioxide in one portion and the mixture stirred at room temperature overnight or until the reaction was complete as evidenced by thin-layer chromatography. The mixture was then filtered and the solvent evaporated to provide the title compound in quantitative yield. 1H-NMR(CDCl3)ppm(delta): 1.6 (d, 3H), 2.7-3.6 (m, 1H), 5.1 (m, 2H), 6.8 (d, 1H), 7.6 (m, 2H), 9.8 (s, 1H). The mixture was then filtered the solvent evaporated

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

Procedure: To a solution of 853 mg (4.14 mmole) ethyl 2-methyl-2,3-dihydrobenzofuran-5-carboxylate in 9 ml dry tetrahydrafuran under nitrogen was added 157 mg (4.14 mmole) lithium aluminum hydride in portions and the resulting mixture was stirred at room temperature overnight. The mixture was worked up as described in Preparation A, Part (v), to afford 752 mg of product. The NMR spectrum showed the presence of a band at 4.5 ppm, characteristic of a benzyl alcohol CH2 group. TLC with 1:1 hexane/ethyl ether showed one spot at Rf 0.2 (vanillin spray).

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

Procedure: To a magnetically stirred solution of 680 mg (4.14 mmole) 5-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran in 100 ml methylene dichloride was added 5.44 g manganese dioxide in one portion and the mixture stirred at room temperature overnight or until the reaction was complete as evidenced by thin-layer chromatography. The mixture was then filtered and the solvent evaporated to provide the title compound in quantitative yield. 1H-NMR(CDCl3)ppm(delta): 1.6 (d, 3H), 2.7-3.6 (m, 1H), 5.1 (m, 2H), 6.8 (d, 1H), 7.6 (m, 2H), 9.8 (s, 1H). The mixture was then filtered the solvent evaporated