3-(2-methyl-1,3-dioxolan-2-yl)propanal

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

Procedure: To a solution of 5-2 (44.74 g, 0.22 mol) in 400 mL THF at −78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether was added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 4-3 as a colorless oil. followed by the removal of the cooling bath After stirring for 1 h the organic portion was separated dried over Na2SO4 Evaporative removal of the solvent

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

Procedure: To a solution of 2-2 (44.74 g, 0.22 mol) in 400 mL THF at -78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether were added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 2-3 as a colorless oil. TLC Rf =0.80 (silica, ethyl acetate). 1H NMR (300 MHz, CDCl3) δ 9.73 (s, 1H), 3.50 (d, 1H, J=16 Hz), 2.61 (d, 1H, J=21 Hz), 2.48 (m, 1H), 2.07 (t, 1H, J=7H), 1.33 (s, 3H). followed by the removal of the cooling bath After stirring for 1 h the organic portion was separated dried over Na2SO4 Evaporative removal of the solvent

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

Procedure: To a solution of 2-2 (44.74 g, 0.22 mol) in 400 mL THF at -78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether were added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 2-3 as a colorless oil. TLC Rf =0.80 (silica, ethyl acetate). 1H NMR (300 MHz, CDCl3) δ 9.73 (s, 1H), 3.50 (d, 1H, J=16 Hz), 2.61 (d, 1H, J=21 Hz), 2.48 (m, 1H), 2.07 (t, 1H, J=7H), 1.33 (s, 3H). followed by the removal of the cooling bath After stirring for 1 h the organic portion was separated dried over Na2SO4 Evaporative removal of the solvent

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

Procedure: To a solution of 5-2 (44.74 g, 0.22 mol) in 400 mL THF at −78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether was added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 4-3 as a colorless oil. followed by the removal of the cooling bath After stirring for 1 h the organic portion was separated dried over Na2SO4 Evaporative removal of the solvent

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

Procedure: To a solution of 5-2 (44.74 g, 0.22 mol) in 400 mL THF at −78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether was added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 4-3 as a colorless oil. followed by the removal of the cooling bath After stirring for 1 h the organic portion was separated dried over Na2SO4 Evaporative removal of the solvent

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

Procedure: To a solution of 2-2 (44.74 g, 0.22 mol) in 400 mL THF at -78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether were added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 2-3 as a colorless oil. TLC Rf =0.80 (silica, ethyl acetate). 1H NMR (300 MHz, CDCl3) δ 9.73 (s, 1H), 3.50 (d, 1H, J=16 Hz), 2.61 (d, 1H, J=21 Hz), 2.48 (m, 1H), 2.07 (t, 1H, J=7H), 1.33 (s, 3H). followed by the removal of the cooling bath After stirring for 1 h the organic portion was separated dried over Na2SO4 Evaporative removal of the solvent

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

Procedure: To a solution of 5-2 (44.74 g, 0.22 mol) in 400 mL THF at −78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether was added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 4-3 as a colorless oil. followed by the removal of the cooling bath After stirring for 1 h the organic portion was separated dried over Na2SO4 Evaporative removal of the solvent