1,3,3a,4,5,6,7,7a-octahydroinden-2-one

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 3.16 g (23 mmol) of (3a alpha, 7a alpha )-octahydro-2H-inden-2-one, 17.3 g (207 mmol) of NaHCO3 and 300 mL of dichloromethane was added 9.29 g of 85% m. chloroperoxybenzoic acid in small portions over 15 min. The reaction mixture was stirred for 17 h at 20° C., then 200 mL of 10% aqueous Na2S2O3 was added and, after 15 min, the organic phase was separated. Extraction of the aqueous portion with 2×100 mL of dichloromethane, washing of the combined organic solutions with 10% Na2CO3 and concentration of the dried (MgSO4) solutions under vacuum 9ave 3.51 9 (95%) of racemic (4a alpha, 8a alpha)-octahydro-3H-2-benzopyran-3-one. TLC Rf 0.40 (SiO2, ethyl ether, iodine-brown). was added 9.29 g of 85% m the organic phase was separated Extraction of the aqueous portion with 2×100 mL of dichloromethane washing of the combined organic solutions with 10% Na2CO3 and concentration of the dried (MgSO4) solutions under vacuum 9ave 3.51 9 (95%) of racemic (4a alpha, 8a alpha)-octahydro-3H-2-benzopyran-3-one

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 33.6 g (155 mmol) of finely ground pyridinium chlorochromate, stirred in 300 mL of dry dichloromethane, was added 7.0 g (50 mmol) of (2 alpha and 2 beta)-octahydro-1H-inden-2-ol in 30 mL of dichloromethane. After stirring for 2 h at 20° C., 300 mL of ether was added, the organic solution decanted from the gummy precipitate and the latter extracted with 5×100 mL of ether. The combined organic solutions were filtered through 450 g of silica gel and the latter washed with ether. Concentration of the filtrates and distillation gave 5.5 g (80%) of (3a alpha, 7a alpha)-octahydro-2H-inden-2-one bp 110°-112° C. (18 mm); TLC Rf of 0.29 (SiO2, dichloromethane, molybdophosphoric acid-colorless on blue-green). the organic solution decanted from the gummy precipitate the latter extracted with 5×100 mL of ether The combined organic solutions were filtered through 450 g of silica gel the latter washed with ether Concentration of the filtrates and distillation

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 3.16 g (23 mmol) of (3a alpha, 7a alpha)-octahydro-2H-inden-2-one, 17.3 g (207 mmol) of NaHCO3 and 300 mL of dichloromethane was added 9.29 g of 85% m. chloroperoxybenzoic acid in small portions over 15 min. The reaction mixture was stirred for 17 h at 20° C., then 200 mL of 10% aqueous Na2S2O3 was added and, after 15 min, the organic phase was separated. Extraction of the aqueous portion with 2×100 mL of dichloromethane, washing of the combined organic solutions with 10% Na2CO3 and concentration of the dried (MgSO4) solutions under vacuum gave 3.51 g (95%) of racemic (4a alpha, 8a alpha)-octahydro-3H-2-benzopyran-3-one. TLC Rf 0.40 (SiO2, ethyl ether, iodine-brown). was added 9.29 g of 85% m the organic phase was separated Extraction of the aqueous portion with 2×100 mL of dichloromethane washing of the combined organic solutions with 10% Na2CO3 and concentration of the dried (MgSO4) solutions under vacuum

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 33.6 g (155 mmol) of finely ground pyridinium chlorochromate, stirred in 300 mL of dry dichloromethane, was added 7.0 g (50 mmol) of (2 alpha and 2 beta)-octahydro-1H-inden-2-ol in 30 mL of dichloromethane. After stirring for 2 h at 20° C., 300 mL of ether was added, the organic solution decanted from the gummy precipitate and the latter extracted with 5×100 mL of ether. The combined organic solutions were filtered through 450 g of silica gel and the latter washed with ether. Concentration of the filtrates and distillation gave 5.5 g (80%) of (3a alpha, 7a alpha)octahydro-2H-inden-2-one bp 110°-112° C. (18 mm); TLC Rf of 0.29 (SiO2, dichloromethane, molybdophosphoric acid-colorless on blue-green). the organic solution decanted from the gummy precipitate the latter extracted with 5×100 mL of ether The combined organic solutions were filtered through 450 g of silica gel the latter washed with ether Concentration of the filtrates and distillation