Diethyl Malonate → Diethyl 2-(2-(benzyloxy)ethyl)malonate

HRID 500059Notes

Reaction equation

HRID 500059 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:14][CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:17]([O:16][CH2:15][CH2:14][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 5360545Sodium

Product 1

HCID 12549951Diethyl 2-(2-(benzyloxy)ethyl)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound was prepared by a modification of the method of Ramalingam et al Tetrahedron, 51, 2875-2894 (1995)]. Thus, sodium (1.20 g) was dissolved in absolute ethanol (25 mL) under argon. Diethyl malonate (14.00 g) was added and the mixture was refluxed for 30 min. Benzyl bromoethyl ether (10 g) was added and the mixture was stirred at reflux for 16 hours. The ethanol was removed by rotary evaporation and the residue was partitioned between ether (100 mL) and water (50 mL). The ethereal layer was washed with water (3×50 mL) and dried over sodium sulfate. The ether was removed by rotary evaporation and the residue was distilled in vacuoo. The fraction distilling at 40-55° C. was discarded (unreacted diethyl malonate). The product distilled at 140-150° C. (1 mm), [lit. bp 138-140 C (1 mm)]. The yield was 12.60 g of colourless oil.

Workup

  1. customThe compound was prepared by a modification of the method of Ramalingam et al Tetrahedron, 51, 2875-2894 (1995)]
  2. temperaturethe mixture was refluxed for 30 min
  3. temperatureat reflux for 16 hours
  4. customThe ethanol was removed by rotary evaporation
  5. customthe residue was partitioned between ether (100 mL) and water (50 mL)
  6. washThe ethereal layer was washed with water (3×50 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe ether was removed by rotary evaporation
  9. distillationthe residue was distilled in vacuoo
  10. distillationThe fraction distilling at 40-55° C.
  11. distillationThe product distilled at 140-150° C. (1 mm), [lit. bp 138-140 C (1 mm)]

Sources & evidence

ORD record
ord-1581d8761c9a49b4886422c20bf3fc40
Source dataset
uspto-grants-2010_08
Patent number
US07767796B2

Reaction notes

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