Triethylamine → 6,8-Bis(methylsulfonyloxymethyl)-1,4-dioxaspiro[4.4]nonane

Temperature

0 °C

6,8-Bis(hydroxymethyl)-1,4-dioxaspiro[4.4]nonane (8.18 g, 43.5 mmol) was dissolved in dichloromethane (200 ml) and chilled to 0° C. To the chilled solution was added 4-dimethylaminopyridine (0.53 g, 4.4 mmol) and distilled triethylamine (18.2 ml, 131 mmol). Then methanesulfonyl chloride (7.41 ml, 11.0 g, 95.7 mmol) was added drop-wise via syringe over 10 min and the reaction was allowed to come to ambient temperature and stir for 18 h under nitrogen. The reaction was quenched with saturated sodium bicarbonate (25 ml) and stirred for 30 min. After stirring, the layers were separated and the aqueous phase extracted with dichloromethane (2×50 ml). The organics were combined, dried over sodium sulfate, filtered and concentrated to yield a reddish brown oil (14.9, 99.4%).

1. customto come to ambient temperature
2. customThe reaction was quenched with saturated sodium bicarbonate (25 ml)
3. stirringstirred for 30 min
4. stirringAfter stirring
5. customthe layers were separated
6. extractionthe aqueous phase extracted with dichloromethane (2×50 ml)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto yield a reddish brown oil (14.9, 99.4%)

ORD record

ord-898cbbbecf204c9288f884fbe3620e7b

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897611B2