Triethylamine → Bicyclo[2.2.1]hept-5-ene-2-ethanol
Reaction equation
C(N([CH2:6][CH3:7])CC)C.CO[C:10]1[CH:20]=[CH:19][C:13]([CH:14]=CC(Cl)=O)=[CH:12][CH:11]=1.C([O-])(O)=[O:22].[Na+].[NH4+].[Cl-]>CN(C1C=CN=CC=1)C.ClCCl.[Cl-].[Na+].O>[CH:10]12[CH2:14][CH:13]([CH:12]=[CH:11]1)[CH2:19][CH:20]2[CH2:6][CH2:7][OH:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
NBCH2CH2O2CCH═CHC6H4OMe (EtMeOCinnNB): A 100 mL, 3 neck RBF equipped with a thermowell, addition funnel, and mechanical stirrer was charged with NBCH2OH (2 g, 14.47 mmol), DMAP (88.4 mg, 0.72 mmol, 5 mol %), 10.1 mL triethylamine (72.4 mmol) and 25 mL dichloromethane. The mixture was stirred at room temperature for 45 minutes before the addition of 4-methoxycinnamoyl chloride (3.1 g, 15.9 mmol) in 5 mL dichloromethane from the addition funnel was started. After this addition was completed, the mixture was stirred at 25° C. overnight. After confirmation of complete reaction by GC the reaction mixture was diluted with 20 mL dichloromethane, followed by washes with (2×25 mL) NaHCO3 solution, (2×15 mL) NH4Cl solution, (2×25 mL) brine, dried over Na2SO4 and filtered. Concentration of the filtrate gave 3.9 g of crude product as a colorless, viscous oil (93% crude yield) with 96% crude purity by GC.
Workup
- additionaddition funnel, and mechanical stirrer
- additionAfter this addition
- customAfter confirmation of complete reaction by GC the reaction mixture
- dry with materialdried over Na2SO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-e36ede8a07f84e94af54bd6c146429c6
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09175123B2
Reaction notes
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