Diethyl Malonate → HCID 18007487, compound

HRID 988085Notes

Reaction equation

HRID 988085 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].Br[CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(O)C>[CH3:21][Si:20]([CH3:22])([O:19][CH2:18][CH2:17][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 18007487HCID 18007487, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diethyl malonate (5.14 g, 32.1 mmol) in anhydrous ethyl alcohol (100 mL) was reacted with 96% sodium ethoxide (2.28 g, 32.2 mmol) at 76° C. for 1 h. After the solution cooled to room temperature, (2-bromoethoxy)-tert-butyldimethylsilane (7.68 g, 32.1 mmol) was added. The resulting solution was heated at 76° C. for 15.5 h and then concentrated. The residue was partitioned between dichloromethane and water. The organic layer was dried (Na2SO4) and concentrated to give the title compound as a brown oil (10.22 g, 100%). 1H NMR (CDCl3) δ 4.19-4.11 (m, 4H), 3.62 (t, 2H, J=6.0 Hz), 3.55 (t, 1H, J=7.3 Hz), 2.10-2.06 (m, 2H), 1.23 (t, 6H, J=7.1 Hz), 0.85 (s, 9H), 0.01 (s, 6H).

Workup

  1. temperatureThe resulting solution was heated at 76° C. for 15.5 h
  2. concentrationconcentrated
  3. customThe residue was partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7be48f08548e4a47ba7f8848af791614
Source dataset
uspto-grants-2003_10
Patent number
US06635637B2

Reaction notes

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