Sodium Hydroxide → 3-Ethyloxetane-3-carboxylic acid

(3-Ethyloxetan-3-yl)methanol (0.58 g, 5.00 mmol) was dissolved in 10 mL of a 1:1 ACN-water mixture, and bis-acetoxyiodobenzene (BAIB, 3.54 g, 11.0 mmol) was added. The mixture was cooled in an ice bath, and TEMPO (0.156 g, 1.00 mmol) was added under argon flow. The mixture was stirred at room temperature for 1 hr, and then treated with 1 M aqueous sodium hydroxide (20 mL). The solution was washed twice with EtOAc and then acidified to pH 2. The aqueous solution was extract six times with EtOAc and these combined extracts were dried over sodium sulfate and concentrated to afford 0.37 g (57%) of Intermediate 55 as oil, which was used without further purification.

1. temperatureThe mixture was cooled in an ice bath
2. washThe solution was washed twice with EtOAc
3. extractionThe aqueous solution was extract six times with EtOAc
4. dry with materialthese combined extracts were dried over sodium sulfate
5. concentrationconcentrated

ORD record

ord-0ca3d4aaf1bf470590faafe9af906ffd

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148380B2