Diethyl Ether → HCID 59707722, compound

HRID 1916000Notes

Reaction equation

HRID 1916000 reaction equation
[C:1]([O:6][CH2:7][CH2:8][N:9](C)C)(=[O:5])[C:2]([CH3:4])=[CH2:3].[Br:12]CC(OC(C)(C)C)=O.C(OCC)C>C(#N)C>[Br:12][C:2]([CH3:4])([CH3:3])[C:1]([O:6][CH2:7][CH2:8][NH2:9])=[O:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 17869(Dimethylamino)ethyl methacrylateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 59707722HCID 59707722, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 g 2-(Dimethylamino)ethyl methacrylate and 8.68 g tert-butyl bromoacetate were reacted in 20 ml acetonitrile for 24 h at 50° C. under N2 protection. Upon addition of 250 ml ethyl ether to the reaction mixture, the formed white crystals were isolated and dried. The resulting CB-tBu monomers were immediately stored in a desiccator at −20° C. (yield 96%). 1H NMR (D2O) δ (ppm): 1.44 (s, 9H, —OC(CH3)3), 1.87 (s, 3H, CH2═C(CH3)COO—), 3.31 (s, 6H, —CH2N(CH3)2CH2COO—), 3.98 (t, J=3 Hz, 2H, CH2═C(CH3)COOCH2CH2N(CH3)2CH2—), 4.28 (s, 2H, —CH2N(CH3)2CH2COO—), 4.60 (t, J=3 Hz, 2H, CH2═C(CH3)COOCH2CH2N(CH3)2CH2—), 5.73 and 6.10 (s, 2H, CH2═C(CH3)COO—).

Workup

  1. customthe formed white crystals were isolated
  2. customdried
  3. customThe resulting CB-tBu monomers were immediately stored in a desiccator at −20° C.

Sources & evidence

ORD record
ord-edd6911c9ee940838b238d518e6daa47
Source dataset
uspto-grants-2013_12
Patent number
US08617592B2

Reaction notes

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