Cesium carbonate → Methyl 3-tert-butyl-5-(2-methoxy-1-methoxymethylethoxy)benzoate

Temperature

50 °C

Methyl 3-tert-butyl-5-hydroxybenzoate (O6.043; 2.28 g) and 2-methoxy-l-methoxymethyl-ethyl methanesulfonate (2.93 g) were dissolved in DMF (50 ml), and cesium carbonate (4.82 g) was added. After stirring at 50° C. for 6 h, the mixture was left to stand overnight. After stirring at 50° C. for 4 further hours, one further eq. of cesium carbonate and one further eq. of the mesylate were added, and the mixture was stirred at 50° C. for a further 4 h and left to stand overnight. Then the mixture was stirred at 50° C. for a further 8 h and left to stand for 6 days, and then a further 0.5 eq. of cesium carbonate and mesylate was added. After stirring at 50° C. for a further 8 h, the mixture was left to stand for 5 days, then the DMF was drawn off and the residue was taken up with DCM/water. The DCM phase was removed and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MTB ether gradient 0-50% within 60 min). 2.05 g of the title compound were obtained.

1. waitthe mixture was left
2. waitto stand overnight
3. additionwere added
4. stirringthe mixture was stirred at 50° C. for a further 4 h
5. waitleft
6. waitto stand overnight
7. stirringThen the mixture was stirred at 50° C. for a further 8 h
8. waitleft
9. waitto stand for 6 days
10. stirringAfter stirring at 50° C. for a further 8 h
11. waitthe mixture was left
12. waitto stand for 5 days
13. customThe DCM phase was removed
14. concentrationconcentrated
15. customThe residue was purified
16. customsilica gel (120 g cartridge, n-heptane/MTB ether gradient 0-50% within 60 min)

ORD record

ord-5aa3a669f75e49978baddb3f2ae32a9f

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076336B2