pentane-1,1-diol

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

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

Procedure: Allyl bromide (2.5 mL, 0.029 mol) was added dropwise to the mixture of 1,5-pentanediol (3 g, 0.029 mol) and sodium hydride (1.2 g, 80% dispersion in oil) in dry dimethylformamide. Stirring was continued overnight at room temperature. T.l.c. (2:1-toluene and ethyl acetate) still indicated the presence of some unreacted pentanediol. The unreacted sodium hydride was destroyed by addition of methanol. The mixture was concentrated to 50 mL by evaporation in vacuo. After dilution with methylene chloride (150 mL), the solvents were washed with water (three times), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant. The appropriate fractions gave compound 229 (0.931 g, 30%). 1H-n.m.r. (CDCl3): 5.83 (m, 1 H, --CH=), 5.20 (m, 2 H, =CH2), 3.95 (dd, 1 H, J=5.5 and 1.0 Hz, allylics), 3.66 and 3.46 (two t, 2 H each, J=6.5 Hz, O--CH2), 1.64 (m, 4 H) and 1.44 (m, 2 H): methylenes); 13C-n.m.r. (CDCl3): 134.7 and 116.6 (ethylenics), 71.6, 70.1 (CH2 --O--CH2), 62.1 (CH2OH) 32.2, 29.2 and 22.2 (methylenes). The unreacted sodium hydride was destroyed by addition of methanol The mixture was concentrated to 50 mL by evaporation in vacuo After dilution with methylene chloride (150 mL), the solvents were washed with water (three times) dried over magnesium sulfate evaporated in vacuo The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant

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

Procedure: Allyl bromide (2.5 mL, 0.029 mol) was added dropwise to the mixture of 1,5-pentanediol (3 g, 0.029 mol) and sodium hydride (1.2 g, 80% dispersion in oil) in dry dimethylformamide. Stirring was continued overnight at room temperature. T.l.c. (2:1-toluene and ethyl acetate) still indicated the presence of some unreacted pentanediol. The unreacted sodium hydride was destroyed by addition of methanol. The mixture was concentrated to 50 mL by evaporation in vacuo. After dilution with methylene chloride (150 mL), the solvents were washed with water (three times), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant. The appropriate fractions gave compound 229 (0.931 g, 30%). 1H-n.m.r. (CDCl3): 5.83 (m, 1 H, --CH=), 5.20 (m, 2 H, =CH2), 3.95 (dd, 1 H, J=5.5 and 1.0 Hz, allylics), 3.66 and 3.46 (two t, 2 H each, J=6.5 Hz, O--CH2), 1.64 (m, 4 H) and 1.44 (m, 2 H): methylenes); 13C-n.m.r. (CDCl3): 134.7 and 116.6 (ethylenics), 71.6, 70.1 (CH2 --O--CH2), 62.1 (CH2OH) 32.2, 29.2 and 22.2 (methylenes). The unreacted sodium hydride was destroyed by addition of methanol The mixture was concentrated to 50 mL by evaporation in vacuo After dilution with methylene chloride (150 mL), the solvents were washed with water (three times) dried over magnesium sulfate evaporated in vacuo The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant

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

Procedure: To a solution of pentanediol (1 mmol) in THF (5 ml) was added a catalytic amount of dimethyltin dichloride (0.01 mmol), solid K2CO3 (2.0 mmol) and benzoyl chloride (1.2 mmol), at room temperature. After stirring the mixture at room temperature until the diol disappeared (checked by TLC), the mixture was poured onto water and the organic portion was extracted with DCM. After evaporation of the solvent, a residue was obtained and purified by flash chromatography using a mixture of DCM/MeOH as eluent. at room temperature the mixture was poured onto water the organic portion was extracted with DCM After evaporation of the solvent a residue was obtained purified by flash chromatography a mixture of DCM/MeOH as eluent

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

Procedure: Allyl bromide (2.5 mL, 0.029 mol) was added dropwise to the mixture of 1,5-pentanediol (3 g, 0.029 mol) and sodium hydride (1.2 g, 80% dispersion in oil) in dry dimethylformamide. Stirring was continued overnight at room temperature. T.l.c. (2:1-toluene and ethyl acetate) still indicated the presence of some unreacted pentanediol. The unreacted sodium hydride was destroyed by addition of methanol. The mixture was concentrated to 50 mL by evaporation in vacuo. After dilution with methylene chloride (150 mL), the solvents were washed with water (three times), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant. The appropriate fractions gave compound 229 (0.931 g, 30%). 1H-n.m.r. (CDCl3): 5.83 (m, 1 H, --CH=), 5.20 (m, 2 H, =CH2), 3.95 (dd, 1 H, J=5.5 and 1.0 Hz, allylics), 3.66 and 3.46 (two t, 2 H each, J=6.5 Hz, O--CH2), 1.64 (m, 4 H) and 1.44 (m, 2 H): methylenes); 13C-n.m.r. (CDCl3): 134.7 and 116.6 (ethylenics), 71.6, 70.1 (CH2 --O--CH2), 62.1 (CH2OH) 32.2, 29.2 and 22.2 (methylenes). The unreacted sodium hydride was destroyed by addition of methanol The mixture was concentrated to 50 mL by evaporation in vacuo After dilution with methylene chloride (150 mL), the solvents were washed with water (three times) dried over magnesium sulfate evaporated in vacuo The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant

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

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ninety-eight grams (1 mol) of maleic anhydride were weighed into a 500 ml. round-bottom flask fitted with a separatory funnel, thermometer and reflux condenser. One hundred and two grams (1 mol) of 1, 5 - pentanediol were introduced into the separatory funnel. The maleic anhydride was heated to 140° C by means of a heating mantle and the pentanediol was added dropwise over a period of 60 minutes. The reactants were stirred with a magnetic stirrer. The temperature was raised gradually to 160° C. After the addition of the pentanediol was complete, the mixtures was heated an additional 30 minutes, then allowed to cool. The monoester was a moderately viscous liquid of 1400 - 1500 centipoise and an acid value of 216. round-bottom flask fitted with a separatory funnel thermometer and reflux condenser the mixtures was heated an additional 30 minutes to cool

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

Procedure: To a solution of pentanediol (1 mmol) in THF (5 ml) was added a catalytic amount of dimethyltin dichloride (0.01 mmol), solid K2CO3 (2.0 mmol) and benzoyl chloride (1.2 mmol), at room temperature. After stirring the mixture at room temperature until the diol disappeared (checked by TLC), the mixture was poured onto water and the organic portion was extracted with DCM. After evaporation of the solvent, a residue was obtained and purified by flash chromatography using a mixture of DCM/MeOH as eluent. at room temperature the mixture was poured onto water the organic portion was extracted with DCM After evaporation of the solvent a residue was obtained purified by flash chromatography a mixture of DCM/MeOH as eluent

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

Procedure: Allyl bromide (2.5 mL, 0.029 mol) was added dropwise to the mixture of 1,5-pentanediol (3 g, 0.029 mol) and sodium hydride (1.2 g, 80% dispersion in oil) in dry dimethylformamide. Stirring was continued overnight at room temperature. Tol.c. (2:1 - toluene and ethyl acetate) still indicated the presence of some unreacted pentanediol. The unreacted sodium hydride was destroyed by addition of methanol. The mixture was concentrated to 50 mL by evaporation in vacuo. After dilution with methylene chloride (150 mL), the solvents were washed with water (three times), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant. The appropriate fractions gave compound 29 (0.931 g, 30%). 1H-n.m.r. (CDCl3): 5.83 (m, 1H, --CH=), 5.20 (m, 2H, =CH2), 3.95 (dd, 1H, J=5.5 and 1.0 Hz, allylics), 3.66 and 3.46 (two t, 2H each, J=6.5 Hz, O--CH2), 1.64 (m, 4H) and 1.44 (m, 2H): methylenes); 13C-n.m.r.(CDCl3): 134.7 and 116.6 (ethylenics), 71.6, 70.1 (CH2 --O--CH2), 62.1 (CH2OH) 32.2, 29.2 and 22.2 (methylenes). The unreacted sodium hydride was destroyed by addition of methanol The mixture was concentrated to 50 mL by evaporation in vacuo After dilution with methylene chloride (150 mL), the solvents were washed with water (three times) dried over magnesium sulfate evaporated in vacuo The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant

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

Procedure: To a solution of pentanediol (1 mmol) in THF (5 ml) was added a catalytic amount of dimethyltin dichloride (0.01 mmol), solid K2CO3 (2.0 mmol) and benzoyl chloride (1.2 mmol), at room temperature. After stirring the mixture at room temperature until the diol disappeared (checked by TLC), the mixture was poured onto water and the organic portion was extracted with DCM. After evaporation of the solvent, a residue was obtained and purified by flash chromatography using a mixture of DCM/MeOH as eluent. at room temperature the mixture was poured onto water the organic portion was extracted with DCM After evaporation of the solvent a residue was obtained purified by flash chromatography a mixture of DCM/MeOH as eluent

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

Procedure: Allyl bromide (2.5 mL, 0.029 mol) was added dropwise to the mixture of 1,5-pentanediol (3 g, 0.029 mol) and sodium hydride (1.2 g, 80% dispersion in oil) in dry dimethylformamide. Stirring was continued overnight at room temperature. T.l.c. (2:1-toluene and ethyl acetate) still indicated the presence of some unreacted pentanediol. The unreacted sodium hydride was destroyed by addition of methanol. The mixture was concentrated to 50 mL by evaporation in vacuo. After dilution with methylene chloride (150 mL), the solvents were washed with water (three times), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant. The appropriate fractions gave compound 229 (0.931 g, 30%). 1H-n.m.r. (CDCl3): 5.83 (m, 1 H, --CH=), 5.20 (m, 2 H, =CH2), 3.95 (dd, 1 H, J=5.5 and 1.0 Hz, allylics), 3.66 and 3.46 (two t, 2 H each, J=6.5 Hz, O--CH2), 1.64 (m, 4 H) and 1.44 (m, 2 H): methylenes); 13C-n.m.r. (CDCl3): 134.7 and 116.6 (ethylenics), 71.6, 70.1 (CH2 --O--CH2), 62.1 (CH2OH) 32.2, 29.2 and 22.2 (methylenes). The unreacted sodium hydride was destroyed by addition of methanol The mixture was concentrated to 50 mL by evaporation in vacuo After dilution with methylene chloride (150 mL), the solvents were washed with water (three times) dried over magnesium sulfate evaporated in vacuo The residue was chromatographed on silica gel using a 2:1 mixture of toluene and ethyl acetate as eluant