Iodoethane → 2-Ethoxy-3-trifluoromethoxybenzaldehyde
Reaction equation
[OH:1][C:2]1[C:9]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].I[CH2:22][CH3:23]>CN(C=O)C>[CH2:22]([O:1][C:2]1[C:9]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 37 °C
Procedure
To a solution of 2-hydroxy-3-trifluoromethoxybenzaldehyde (1.00 g, 4.82 mmol) in DMF (10 mL), was added K2CO3 (1.46 g, 10.6 mmol) followed by iodoethane (0.57 mL, 7.24 mmol) and the mixture was heated to 37° C. for 6 h. The reaction was quenched by the addition of H2O (40 mL) and the mixture was extracted with EtOAc (3×100 mL). The combined organics were washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (1.17 g, quant.) as an orange oil: 1H NMR (300 MHz, DMSO-d6) δ 10.31 (s, 1H), 7.77 (m, 2H), 7.38 (t, J=8.1 Hz, 1H), 4.19 (q, J=6.9 Hz, 2H), 1.36 (t, J=6.9 Hz, 3H).
Workup
- customThe reaction was quenched by the addition of H2O (40 mL)
- extractionthe mixture was extracted with EtOAc (3×100 mL)
- washThe combined organics were washed with brine (2×100 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-29249f041c0d4bc4839e62a984e08d18
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879872B2
Reaction notes
Loading…