5,5,5-trifluoropentan-1-ol → HCID 22915404, compound

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).

1. filtrationfilter the reaction mixture through Celite®
2. concentrationConcentrate the filtrate in vacuo
3. washwash with 1:1 10% sodium thiosulphate
4. dry with materialDry the organics with anhydrous sodium sulfate
5. filtrationfilter
6. concentrationconcentrate in vacuo

ORD record

ord-77932f4d92174750ba2464430cf5ee45

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436002B2