Cesium carbonate → HCID 86714681, compound

HRID 1409475Notes

Reaction equation

HRID 1409475 reaction equation
[OH:1][CH:2]([CH3:14])[CH2:3][C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:21][Si:22]([CH2:25][CH2:26][O:27][CH2:28]Cl)([CH3:24])[CH3:23]>CC(C)=O>[OH:1][CH:2]([CH3:14])[CH2:3][C:4]1[N:8]([CH2:28][O:27][CH2:26][CH2:25][Si:22]([CH3:24])([CH3:23])[CH3:21])[N:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 86714680HCID 86714680, compound

Product 1

HCID 86714681HCID 86714681, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a flask containing ethyl 5-(2-hydroxypropyl)-1H-pyrazole-3-carboxylate (15.65 mmol, 3.2 g) in acetone (60 ml), Cs2CO3 (13.7 g, 99.1 mmol), SEM-Cl (9.3 ml, 51.6 mmol) were added and stirred at RT overnight. The reaction mixture was quenched by the addition of H2O and extracted with EtOAc. The organic layer was concentrated and purified by column-chromatography. Yield 3.8 g. 1H-NMR (400 MHz; CDCl3): δ −0.05 (s, 9H), 0.89 (t, 2H), 1.25 (d, 3H), 1.40 (t, 3H), 2.71-2.83 (m, 3H), 3.57 (t, 2H), 4.34 (q, 2H), 5.79 (s, 2H), 6.74 (s, 1H). LC-MS: [M+1]=329.14.

Workup

  1. additionwere added
  2. customThe reaction mixture was quenched by the addition of H2O
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified by column-chromatography

Sources & evidence

ORD record
ord-37d975464c1e4d5f846d33aff6a55f33
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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