Tetrahydropyran-2-methanol → Oxane-2-carboxylic acid

(Tetrahydro-2H-pyran-2-yl)methanol (0.51 g, 4.30 mmol) was dissolved in 10 mL of 1:1 ACN/water mixture, and bis-acetoxyiodobenzene [BAIB] (3.04 g, 9.46 mmol) was added to the mixture. It was then cooled to 0 C in an ice bath, and TEMPO (0.134 g, 0.86 mmol) was added under argon flow. The mixture was stirred at room temperature for 3 hours, and the reaction was quenched by addition of 2×20 mL of 1 M NaOH. Basic solution was washed 3×30 mL of EtOAc, and re-acidified with 1 M HCl to ca. pH 2. Aqueous layer was then extracted 6×30 mL of EtOAc, organic layers were combined, dried over sodium sulfate and evaporated. The title compound was isolated as an oil (0.34 g, 61%) was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ4.11 (d, 1H, J=10.5 Hz), 3.98 (d, 1H, J=9.9 Hz), 3.53 (m, 1H), 2.10-1.92 (m, 3H), 1.60-1.54 (m, 3H).

1. temperatureIt was then cooled to 0 C in an ice bath
2. customthe reaction was quenched by addition of 2×20 mL of 1 M NaOH
3. washBasic solution was washed 3×30 mL of EtOAc
4. extractionAqueous layer was then extracted 6×30 mL of EtOAc, organic layers
5. dry with materialdried over sodium sulfate
6. customevaporated

ORD record

ord-be8d73a8b3774ce8ab85b35a3b35823a

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148380B2