Ethyl Acetate → HCID 86671864, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Br:8])[CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH2:17]1[CH2:25][O:24][C:23]2[C:19](=[C:20]([CH:26]=[O:27])[S:21][CH:22]=2)[O:18]1.CCOC(C)=O>C1COCC1.O>[Br:8][C:4]1[CH:3]=[C:2]([CH2:1][CH:26]([C:20]2[S:21][CH:22]=[C:23]3[O:24][CH2:25][CH2:17][O:18][C:19]=23)[OH:27])[CH:7]=[CH:6][N:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
4-Methyl-2-bromopyridine (450 mg, 2.62 mmol) was dissolved in anhyd THF (10 mL) and the resulting mixture was cooled to −78° C. LDA (1.76 mL, 1.8 M solution in THF, 3.17 mmol) was added dropwise and the resulting mixture was stirred for 1 h at the same temperature. A solution of 3,4-ethylenedioxythiophene-2-carboxaldehyde (500 mg, 2.94 mmol) in THF (20 mL) was added and the resulting mixture was stirred for 30 min at room temperature. AcOEt (120 mL) and water (120 mL) were added and the layers were separated. The organic layer was washed with water (2×150 mL), dried (Na2SO4) and the solvent was removed by rotary evaporation. Flash chromatography of the residue (silica gel, petroleum ether/AcOEt 1:1) afforded (9) as a yellow oil (850 mg, 2.48 mmol, 95%). 1H NMR (500 MHz, CDCl3) δ 8.23 (d, J=5.0 Hz, 1H), 7.38 (s, 1H), 7.10 (d, J=5.0 Hz, 1H), 6.29 (s, 1H), 5.18 (t, J=6.7 Hz, 1H), 4.20-4.05 (m, 4H), 3.20-2.95 (m, 2H).
Workup
- stirringthe resulting mixture was stirred for 30 min at room temperature
- customthe layers were separated
- washThe organic layer was washed with water (2×150 mL)
- dry with materialdried (Na2SO4)
- customthe solvent was removed by rotary evaporation
Sources & evidence
- ORD record
- ord-aff1c1e608124d07b89b5700f781cb48
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359334B2
Reaction notes
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