Ethyl Bromide → (Z)-2-(Ethoxymethylene)-4,4-dimethylpentanal
Reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][CH2:4][CH:5]=[O:6].C[O-].[Na+].C([O:14][CH3:15])=O.Br[CH2:17][CH3:18]>C1COCC1.C1C=CC=CC=1.CN(C=O)C.O.CO>[CH2:17]([O:6]/[CH:5]=[C:4](/[CH2:3][C:2]([CH3:8])([CH3:7])[CH3:1])\[CH:15]=[O:14])[CH3:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 40 °C
Procedure
4,4-Dimethylpentanal (4.20 g, 36.8 mmol, Step 2) in 36 mL of THF was added over 4 hours by syringe pump to a solution of sodium methoxide, 25 wt. % in methanol (15.1 ml, 66.2 mmol), 15 mL of methanol, and methyl formate (166 ml, 2685 mmol). Following the addition, the reaction was diluted with benzene (50 mL) and DMF (40 mL). The solvents were distilled off at 90° C. leaving the DMF and residual benzene. Bromoethane (11.0 ml, 147 mmol) was added and the solution was heated at 40° C. for 48 hrs and then cooled. The solution was diluted with water, and the reaction was extracted with ether. The combined organic layers were washed with water, brine, and dried over magnesium sulfate, filtered and concentrated to afford the title compound.
Workup
- additionthe addition
- distillationThe solvents were distilled off at 90° C.
- customleaving the DMF and residual benzene
- temperaturecooled
- extractionthe reaction was extracted with ether
- washThe combined organic layers were washed with water, brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-eb84180e3bfe45c0bacc1f37a160b4b3
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633315B2
Reaction notes
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