2-methyl-3-(oxan-2-yloxy)propan-1-ol

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

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

Procedure: A solution of 2-methyl-3-tetrahydropyranyloxy-1-propanol (250 mg; 1.4 mmol) in dichloromethane (4 ml) was added to a suspension of pyridinium chlorochromate (500 mg; 2.32 mmol) and celite (2.5 g) in dichloromethane (10 ml), and stirred at room temperature for 3 hours. Ether (100 ml) was added thereto. The resultant mixture was filtered, and the filtrate was distilled under reduced pressure to give the solvent. The residue was purified by silica gel chromatography using a mixture of ethyl acetate and benzene (1:4) to give 2-methyl-3-tetrahydropyranyloxypropanal (178 mg; yield, 73%). The resultant mixture was filtered the filtrate was distilled under reduced pressure to give the solvent The residue was purified by silica gel chromatography a mixture of ethyl acetate and benzene (1:4)

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

Procedure: 1-Benzoyloxy-2-methyl-3-tetrahydropyranyloxypropane (460 mg; 1.65 mmol) was dissolved in methanol (10 ml), and 1M sodium hydroxide solution (3 ml) and water (10 ml) were added thereto, and the resultant mixture was stirred at room temperature for 5 hours. The reaction mixture was extracted with ethyl acetate. The extracts were washed with water and dried over anhydrous magnesium sulfte. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography using a mixture of ethyl acetate and benzene (1:4) to give 2-methyl-3-tetrahydropyranyloxy-1-propanol (254 mg; yield, 88%). The reaction mixture was extracted with ethyl acetate The extracts were washed with water dried over anhydrous magnesium sulfte The solvent was removed by distillation the residue was purified by silica gel column chromatography a mixture of ethyl acetate and benzene (1:4)

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: Into a 50-mL 3-necked round-bottom flask was placed 2-methylpropane-1,3-diol (20 g, 221.92 mmol, 1.00 equiv) and 4-methylbenzene-1-sulfonic acid (11 mg, 0.06 mmol). Then 3,4-dihydro-2H-pyran (5 g, 59.44 mmol, 0.27 equiv) was added at 0° C. The resulting solution was stirred for 3 h at room temperature. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). Purification afforded 6.9 g (18%) of 2-methyl-3-(oxan-2-yloxy)propan-1-ol as a light yellow liquid. Into a 50-mL 3-necked round-bottom flask was placed Purification

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

Procedure: A solution of 2-methyl-3-tetrahydropyranyloxy-1-propanol (250 mg; 1.4 mmol) in dichloromethane (4 ml) was added to a suspension of pyridinium chlorochromate (500 mg; 2.32 mmol) and celite (2.5 g) in dichloromethane (10 ml), and stirred at room temperature for 3 hours. Ether (100 ml) was added thereto. The resultant mixture was filtered, and the filtrate was distilled under reduced pressure to give the solvent. The residue was purified by silica gel chromatography using a mixture of ethyl acetate and benzene (1:4) to give 2-methyl-3-tetrahydropyranyloxypropanal (178 mg; yield, 73%). The resultant mixture was filtered the filtrate was distilled under reduced pressure to give the solvent The residue was purified by silica gel chromatography a mixture of ethyl acetate and benzene (1:4)

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

Procedure: 1-Benzoyloxy-2-methyl-3-tetrahydropyranyloxypropane (460 mg; 1.65 mmol) was dissolved in methanol (10 ml), and 1M sodium hydroxide solution (3 ml) and water (10 ml) were added thereto, and the resultant mixture was stirred at room temperature for 5 hours. The reaction mixture was extracted with ethyl acetate. The extracts were washed with water and dried over anhydrous magnesium sulfte. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography using a mixture of ethyl acetate and benzene (1:4) to give 2-methyl-3-tetrahydropyranyloxy-1-propanol (254 mg; yield, 88%). The reaction mixture was extracted with ethyl acetate The extracts were washed with water dried over anhydrous magnesium sulfte The solvent was removed by distillation the residue was purified by silica gel column chromatography a mixture of ethyl acetate and benzene (1:4)

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

Procedure: Into a 50-mL 3-necked round-bottom flask was placed 2-methylpropane-1,3-diol (20 g, 221.92 mmol, 1.00 equiv) and 4-methylbenzene-1-sulfonic acid (11 mg, 0.06 mmol). Then 3,4-dihydro-2H-pyran (5 g, 59.44 mmol, 0.27 equiv) was added at 0° C. The resulting solution was stirred for 3 h at room temperature. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). Purification afforded 6.9 g (18%) of 2-methyl-3-(oxan-2-yloxy)propan-1-ol as a light yellow liquid. Into a 50-mL 3-necked round-bottom flask was placed Purification

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

Procedure: A solution of 2-methyl-3-tetrahydropyranyloxy-1-propanol (250 mg; 1.4 mmol) in dichloromethane (4 ml) was added to a suspension of pyridinium chlorochromate (500 mg; 2.32 mmol) and celite (2.5 g) in dichloromethane (10 ml), and stirred at room temperature for 3 hours. Ether (100 ml) was added thereto. The resultant mixture was filtered, and the filtrate was distilled under reduced pressure to give the solvent. The residue was purified by silica gel chromatography using a mixture of ethyl acetate and benzene (1:4) to give 2-methyl-3-tetrahydropyranyloxypropanal (178 mg; yield, 73%). The resultant mixture was filtered the filtrate was distilled under reduced pressure to give the solvent The residue was purified by silica gel chromatography a mixture of ethyl acetate and benzene (1:4)

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

Procedure: 1-Benzoyloxy-2-methyl-3-tetrahydropyranyloxypropane (460 mg; 1.65 mmol) was dissolved in methanol (10 ml), and 1M sodium hydroxide solution (3 ml) and water (10 ml) were added thereto, and the resultant mixture was stirred at room temperature for 5 hours. The reaction mixture was extracted with ethyl acetate. The extracts were washed with water and dried over anhydrous magnesium sulfte. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography using a mixture of ethyl acetate and benzene (1:4) to give 2-methyl-3-tetrahydropyranyloxy-1-propanol (254 mg; yield, 88%). The reaction mixture was extracted with ethyl acetate The extracts were washed with water dried over anhydrous magnesium sulfte The solvent was removed by distillation the residue was purified by silica gel column chromatography a mixture of ethyl acetate and benzene (1:4)