2-(Dimethylamino)ethanol → HCID 84649317, compound
Reaction equation
C([Zn]CC)C.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:12][N:13](CCO)C.C1C[O:21][CH2:20][CH2:19]1>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:7]([C:8]1[N:13]=[CH:12][C:11]([C:20](=[O:21])[CH3:19])=[CH:10][CH:9]=1)[CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
(IM15) (3.596 g, 23.11 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1.694 g, 2.315 mmol) in THF (100 mL) under N2. A 1 M solution of diethyl zinc in hexane (35 mL, 35 mmol) was added drop wise to this mixture followed by N,N-dimethylaminoethanol (0.50 mL, 5.0 mmol). The mixture was heated to reflux for 30 minutes. The mixture was cooled to room temperature and then quenched by the addition of saturated aqueous NH4Cl solution (100 mL). The mixture was filtered through a plug of celite. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with water, brine and then dried over Mg2SO4. Flash Chromatography (120 g silica, 0-40% EtOAc in heptanes) gave the title compound as a yellow oil (0.699 g, 20%) sufficiently pure for the next step.
Workup
- temperatureThe mixture was heated
- temperatureto reflux for 30 minutes
- customquenched by the addition of saturated aqueous NH4Cl solution (100 mL)
- filtrationThe mixture was filtered through a plug of celite
- extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
- washThe combined organic layers were washed with water, brine
- dry with materialdried over Mg2SO4
Sources & evidence
- ORD record
- ord-618a8a06c1e94ac98d0fe69b3f7741d2
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09050327B2
Reaction notes
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