Bis(2-bromoethyl) ether → Ethyl 4-(4-fluorophenyl)-tetrahydro-2H-pyran-4-carboxylate
Reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br>CN1C(=O)CCC1.CCOCC>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:8][CH:9]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of NaH (1.7 g, 71 mmol) in 100 mL NMP stirred at 0° C., was treated dropwise with a mixture of ethyl 2-(4-fluorophenyl)acetate (5.2 g, 29 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (6.6 g, 29 mmol) in 20 mL ether. The mixture was allowed to warm to room temperature and stirred for 5 hours, M+1=253. The mixture was then carefully quenched with 100 mL H2O, and the pH was adjusted to 5. The mixture was extracted with ether (3×100 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (20 mL). The combined organic layers were then dried over anhydrous Na2SO4 and concentrated in vacuo to give 7.1 g of the crude product as a pale yellow oil. MS (m/z)=253 (M+H)+.
Workup
- temperatureto warm to room temperature
- stirringstirred for 5 hours
- customThe mixture was then carefully quenched with 100 mL H2O
- extractionThe mixture was extracted with ether (3×100 mL)
- washThe combined organic layers were washed with H2O (3×50 mL) and brine (20 mL)
- dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b4905368c31e41f3a5b259b08857387d
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635715B2
Reaction notes
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