Reaction #985309

ord-12cd4769e61243bbb6ce182511a8e4f3

Reaction equation

CCCCCCSc1nc(C)cc(C(OCC)OCC)n1
4-Diethoxymethyl-2-hexylsulfanyl-6-methyl-pyrimidine
O=S(=O)(O)O
H2SO4
O=C([O-])[O-].[Na+].[Na+]
Na2CO3
→
CCCCCCSc1nc(C)cc(C=O)n1
yellow oil
Yield 74.0%
CCCCCCSc1nc(C)cc(C=O)n1
2-Hexylsulfanyl-6-methyl-pyrimidine-4-carbaldehyde
Yield 74.0%

Reactants

CCCCCCSc1nc(C)cc(C(OCC)OCC)n1
4-Diethoxymethyl-2-hexylsulfanyl-6-methyl-pyrimidine
O=S(=O)(O)O
H2SO4
O=C([O-])[O-].[Na+].[Na+]
Na2CO3

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionextracted with ethyl acetate
  2. 2
    OtherThe crude oil was purified by silica gel chromatography with a heptane/DCM gradient of 100:0 to 67:33

Procedure

4-Diethoxymethyl-2-hexylsulfanyl-6-methyl-pyrimidine(19 g, 60.8 mmol) was dissolved in THF (100 mL) and 4 N aqueous H2SO4 (100 mL) and heated at 50° C. for 33 h. Poured in cold 10% Na2CO3 solution (400 mL) and extracted with ethyl acetate and a sat. solution of NaCl. The crude oil was purified by silica gel chromatography with a heptane/DCM gradient of 100:0 to 67:33. One obtained 10.7 g (74%) of a yellow oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07351700B2uspto-grants-2008_04