2,3-dihydro-1H-inden-2-ol

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:

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

Procedure: To a mixture of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol (318 mg), 2-hydroxyindane (268 mg), tributylphosphine (405 mg) and tetrahydrofuran (10 ml) was added 1,1′-(azodicarbonyl)dipiperidine (400 mg) at room temperature, and the resulting mixture was stirred for 1 hour. After the reaction mixture was concentrated, the residue was subjected to silica gel column chromatography, and 4-(4-chlorophenyl)-5-[3-(5-indanyloxy)propyl]-2-(2-methyl-1-imidazolyl)oxazole was obtained as an oil (418 mg, 96%) from an ethyl acetate-hexane (1:1, v/v)-eluted fraction. After the reaction mixture was concentrated

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

Procedure: To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15° C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90°-93°/3 mmHg; nD23 =1.5837. extracted by addition of 450 mL of chloroform and 500 g of ice The organic layer was washed twice with water dried over Na2SO4 The solvent was evaporated in vacuo leaving a brown semi-solid The product was distilled rapidly in vacuo

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 slurry of 6.7 g (0.05 moles) of 2-indanol in 75 ml acetic anhydride was cooled to -15°C (ice-acetone bath) and treated with 0.2 ml of 98% sulfuric acid. In about 10 minutes the solid had completely dissolved. The stirred and cooled mixture was then treated over 15 min with a cold solution of 3.6 ml (5.0 g) of 70% nitric acid in 125 ml of acetic anhydride. The mixture was stored at -20°C overnight, then poured into 1 kg of crushed ice. The mixture was stirred until the ice had completely melted and most of the anhydride had reacted. The mixture was extracted with 500 ml of hexane. The organics were washed with saturated bicarbonate and evaporated to 3.0 g of an oil which solidified on standing. Trituration with hexane and recrystallization from the same solvent gave 1.1 g of 2-acetoxy-5-nitroindan, mp 84°-85°C. The aqueous from the hexane extraction yielded 5.3 g of an oil on extraction with benzene. All but 0.9 g of this oil went into hot hexane. Cooling to room temperature gave some oil. The mother liquor was decanted and cooled to 5°C overnight to give 2.0 g (35% total) of the 5-nitro compound, mp 82°-84°C. The filtrate was concentrated to 100 ml cooled again and filtered to give another 0.4 g crude 5-nitro, mp 60°-74°C. The mother liquors were concentrated but gave no solid on cooling. Evaporation afforded 2.0 g (22%) of oily 2-acetoxy-4-nitroindan, contaminated with some 4-nitroindene. In about 10 minutes the solid had completely dissolved cooled mixture had reacted The mixture was extracted with 500 ml of hexane The organics were washed with saturated bicarbonate evaporated to 3.0 g of an oil which Trituration with hexane and recrystallization from the same solvent

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

Procedure: A slurry of 6.7 g (0.05 moles) of 2-indanol in 75 ml acetic anhydride was cooled to -15°C (ice-acetone bath) and treated with 0.2 ml of 98% sulfuric acid. In about 10 minutes the solid had completely dissolved. The stirred and cooled mixture was then treated over 15 min with a cold solution of 3.6 ml (5.0 g) of 70% nitric acid in 125 ml of acetic anhydride. The mixture was stored at -20°C overnight, then poured into 1 kg of crushed ice. The mixture was stirred until the ice had completely melted and most of the anhydride had reacted. The mixture was extracted with 500 ml of hexane. The organics were washed with saturated bicarbonate and evaporated to 3.0 g of an oil which solidified on standing. Trituration with hexane and recrystallization from the same solvent gave 1.1 g of 2-acetoxy-5-nitroindan, mp 84°-85°C. The aqueous from the hexane extraction yielded 5.3 g of an oil on extraction with benzene. All but 0.9 g of this oil went into hot hexane. Cooling to room temperature gave some oil. The mother liquor was decanted and cooled to 5°C overnight to give 2.0 g (35% total) of the 5-nitro compound, mp 82°-84°C. The filtrate was concentrated to 100 ml cooled again and filtered to give another 0.4 g crude 5-nitro, mp 60°-74°C. The mother liquors were concentrated but gave no solid on cooling. Evaporation afforded 2.0 g (22%) of oily 2-acetoxy-4-nitroindan, contaminated with some 4-nitroindene. In about 10 minutes the solid had completely dissolved cooled mixture had reacted The mixture was extracted with 500 ml of hexane The organics were washed with saturated bicarbonate evaporated to 3.0 g of an oil which Trituration with hexane and recrystallization from the same solvent