Ammonium Chloride → 3,3-Oxetanediethanol

Temperature

0 °C

(3-Ethoxycarbonylmethyl-oxetan-3-yl)-acetic acid ethyl ester (122) (2.3 g, 10 mmol) was dissolved in 20 ml of THF. This solution was cooled down to 0° C. using an ice bath and AlLiH4 (1.1 g, 30 mmol) was added by portions. The reaction mixture was stirred for 4 h at ambient temperature, and then saturated aqueous solution of ammonium chloride (20 mL) was added. THF was evaporated off under reduced pressure, then the reaction mixture was taken up in ethyl acetate. The organic phase was separated from the aqueous phase. This extraction was repeated one more time and then the organic phases were combined and washed with brine (100 mL), dried over MgSO4, filtered, and concentrated to give the product (123) (1.3 g, 8.9 mmol, yield: 89%). ESI-MS (M+1): 147 calc. for C7H14O3 146.

1. customTHF was evaporated off under reduced pressure
2. customThe organic phase was separated from the aqueous phase
3. extractionThis extraction
4. washwashed with brine (100 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-3f2197574dca40a8a431b2b95af5ba98

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957073B2