5,5,5-trifluoropentanal

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

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine 5,5,5-trifluoropentanal (2.01 g, 14.35 mmol), 1,4-dioxane (10 mL), selenium dioxide (1.62 g, 1.0 eq), water (0.51 mL), and acetic acid (0.69 mL). Heat the mixture at 90° C. and stir overnight. Allow the reaction mixture to cool to room temperature. Filter, wash the solids with dioxane. Combine the filtrate and washings to give 5,5,5-trifluoro-2-oxopentanal (2.21 g, 100%). GCMS m/z=154. to cool to room temperature Filter wash the solids with dioxane

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

Procedure: Combine 3,3,3-triacetoxy-3-iodophthalide (17.91 g, 1.2 eq) and dichloromethane (95 mL). Add 5,5,5-trifluoro-1-pentanol (5.00 g, 35.18 mmol) in dichloromethane (238 mL) dropwise under nitrogen. After 4 hours, filter the reaction mixture through Celite®. Concentrate the filtrate in vacuo; combine with 50 mL of dichloromethane and wash with 1:1 10% sodium thiosulphate:aqueous sodium hydroxide (1N). Dry the organics with anhydrous sodium sulfate, filter, and concentrate in vacuo to give 5,5,5-trifluoropentanal as a colorless oil (2.13 g, 43%). 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 2.50 (m, 2H), 2.21 (m, 2H), 1.66 (m, 2H). filter the reaction mixture through Celite® Concentrate the filtrate in vacuo wash with 1:1 10% sodium thiosulphate Dry the organics with anhydrous sodium sulfate filter concentrate in vacuo

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine 5,5,5-trifluoropentanal (2.01 g, 14.35 mmol), 1,4-dioxane (10 mL), selenium dioxide (1.62 g, 1.0 eq), water (0.51 mL), and acetic acid (0.69 mL). Heat the mixture at 90° C. and stir overnight. Allow the reaction mixture to cool to room temperature. Filter, wash the solids with dioxane. Combine the filtrate and washings to give the title compound (2.21 g, 100%). GCMS m/z=154. to cool to room temperature Filter wash the solids with dioxane

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

Procedure: Combine 3,3,3-triacetoxy-3-iodophthalide (17.91 g, 1.2 eq) and dichloromethane (95 mL). Add 5,5,5-trifluoro-1-pentanol (5.00 g, 35.18 mmol) in dichloromethane (238 mL) dropwise under nitrogen. After 4 hours, filter the reaction mixture through Celite®. Concentrate the filtrate in vacuo; combine with 50 mL of dichloromethane and wash with 1:1 10% sodium thiosulphate:aqueous sodium hydroxide (1N). Dry the organics with anhydrous sodium sulfate, filter, and concentrate in vacuo to give the title compound as a colorless oil (2.13 g, 43%). 1HNMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 2.50 (m, 2H), 2.21 (m, 2H), 1.66 (m, 2H). filter the reaction mixture through Celite® Concentrate the filtrate in vacuo wash with 1:1 10% sodium thiosulphate Dry the organics with anhydrous sodium sulfate filter concentrate in vacuo