2,4,6-Trimethylpyridine → 2-{1-[(Tert-butyldimethylsilyl)oxy]cyclopropyl}acetaldehyde

Temperatur

0 °C

To a 2.0 L RBF containing 1-(2,2-dimethoxyethyl)cyclopropanol (17.400 g, 119 mmol) was added DCM (550 ml) and the mixture was allowed to stir at 0° C. for 15 min. 2,4,6-Collidine (63.1 ml, 476 mmol) was added and the reaction was allowed to chill for 5 min before the addition of tert-butyldimethylsilyl triflate (27.3 ml, 119 mmol) over 10 min. The reaction was allowed to stir for 20 min and then analyzed by tlc which showed that all of the tertiary alcohol had been protected as its TBS ether. So, triethylsilyl trifluoromethanesulfonate (53.8 ml, 238 mmol) was added via syringe over 10 min. After 20 min, tlc showed all of the material was converted to a baseline Rf material (mixed acetal) and then water (300 mL) was added and the reaction was allowed to stir overnight. The layers were separated. The DCM was washed with dilute HCl to remove the 2,4,6-collidine. The aq. layer was back extracted with DCM. The combined organics were washed with sodium bicarbonate, brine, dried with sodium sulfate and filtered though a plug of silica gel. Desired fractions were collected to give the product.

1. stirringto stir for 20 min
2. waitAfter 20 min
3. stirringto stir overnight
4. customThe layers were separated
5. washThe DCM was washed with dilute HCl
6. customto remove the 2,4,6-collidine
7. extractionThe aq. layer was back extracted with DCM
8. washThe combined organics were washed with sodium bicarbonate, brine
9. dry with materialdried with sodium sulfate
10. filtrationfiltered though a plug of silica gel
11. customDesired fractions were collected
12. customto give the product

ORD-Eintrag

ord-b6fff452a14249f6bfee58e897f547bc

Quelldatensatz

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07973047B2