(2,3-dihydrobenzofuran-2-yl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A three-necked flask is charged with 17 g of lithium aluminum hydride dissolved in anhydrous ethyl ether. 3 g of 2,3-dihydro-2-benzofurancarboxylic acid (Chim. Ler., (1973), 3, p. 259), dissolved in 1,140 ml of ethyl ether, are then introduced. The reaction medium is left stirring overnight. It is then hydrolyzed in an ice bath with 15.2 ml of water, 15.2 ml of 4N sodium hydroxide and then 45.2 ml of water. The complex is drained and washed with ethyl ether and the filtrate is dried and distilled to obtain the expected compound are then introduced The reaction medium is left washed with ethyl ether the filtrate is dried distilled

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

Procedure: A three-necked flask is charged with 17 g of lithium aluminum hydride dissolved in anhydrous ethyl ether. 3 g of 2,3-dihydro-2-benzofurancarboxylic acid (Chim. Ler., (1973), 3, p. 259), dissolved in 1,140 ml of ethyl ether, are then introduced. The reaction medium is left stirring overnight. It is then hydrolyzed in an ice bath with 15.2 ml of water, 15.2 ml of 4N sodium hydroxide and then 45.2 ml of water. The complex is drained and washed with ethyl ether and the filtrate is dried and distilled to obtain the expected compound are then introduced The reaction medium is left washed with ethyl ether the filtrate is dried distilled

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

Procedure: To a mixture of (2,3-dihydro-benzofuran-2-yl)-methanol (1.65 g, 11 mmol), phthalimide (3.24 g, 22 mmol), and triphenylphosphine (5.77 g, 22 mmol) in THF (40 mL) is added diethyl azodicarboxylate (3.46 mL, 22 mmol) at −10° C., and the mixture is allowed to warm to room temperature. After 20 h at rt, the mixture is concentrated in vacuo, and the residue is chromatographed on SiO2 (40% EtOAc in heptane) to afford 2-(2,3-dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione (3.58 g). LCMS: RT=2.64 minutes; MS: 280 (M+H). the mixture is concentrated in vacuo the residue is chromatographed on SiO2 (40% EtOAc in heptane)

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

Procedure: To a mixture of (2,3-dihydro-benzofuran-2-yl)-methanol (1.65 g, 11 mmol), phthalimide (3.24 g, 22 mmol), and triphenylphosphine (5.77 g, 22 mmol) in THF (40 mL) is added diethyl azodicarboxylate (3.46 mL, 22 mmol) at −10° C., and the mixture is allowed to warm to room temperature. After 20 h at rt, the mixture is concentrated in vacuo, and the residue is chromatographed on SiO2 (40% EtOAc in heptane) to afford 2-(2,3-dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione (3.58 g). LCMS: RT=2.64 minutes; MS: 280 (M+H). the mixture is concentrated in vacuo the residue is chromatographed on SiO2 (40% EtOAc in heptane)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A three-necked flask is charged with 17 g of lithium aluminum hydride dissolved in anhydrous ethyl ether. 3 g of 2,3-dihydro-2-benzofurancarboxylic acid (Chim. Ler., (1973), 3, p. 259), dissolved in 1,140 ml of ethyl ether, are then introduced. The reaction medium is left stirring overnight. It is then hydrolyzed in an ice bath with 15.2 ml of water, 15.2 ml of 4N sodium hydroxide and then 45.2 ml of water. The complex is drained and washed with ethyl ether and the filtrate is dried and distilled to obtain the expected compound. are then introduced The reaction medium is left washed with ethyl ether the filtrate is dried distilled

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

Procedure: To a mixture of (2,3-dihydro-benzofuran-2-yl)-methanol (1.65 g, 11 mmol), phthalimide (3.24 g, 22 mmol), and triphenylphosphine (5.77 g, 22 mmol) in THF (40 mL) is added diethyl azodicarboxylate (3.46 mL, 22 mmol) at −10° C., and the mixture is allowed to warm to room temperature. After 20 h at rt, the mixture is concentrated in vacuo, and the residue is chromatographed on SiO2 (40% EtOAc in heptane) to afford 2-(2,3-dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione (3.58 g). LCMS: RT=2.64 minutes; MS: 280 (M+H). the mixture is concentrated in vacuo the residue is chromatographed on SiO2 (40% EtOAc in heptane)