Diethyl Malonate → HCID 53668681, compound

HRID 1602384Notes

Reaction equation

HRID 1602384 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Br[CH2:15][C:16]1[C:21]2[CH:22]=[CH:23][O:24][C:20]=2[C:19]([Cl:25])=[CH:18][CH:17]=1>C1COCC1>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([CH2:15][C:16]1[C:21]2[CH:22]=[CH:23][O:24][C:20]=2[C:19]([Cl:25])=[CH:18][CH:17]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 19611696HCID 19611696, compound

Product 1

HCID 53668681HCID 53668681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl malonate (1.7 ml) was added dropwise to a suspension of sodium hydride (60%; 0.3 g) in dry THF (40 ml) at 0° under nitrogen. The mixture was allowed to warm to room temperature over 15 mins. Then a solution of 4-bromomethyl-7-chloro-benzofuran in dry THF (10 ml) was added in one portion and the mixture stirred for 1 h; then partitioned between water (100 ml) and ethyl acetate (3×50 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4) and evaporated to give the title compound as a pale yellow oil (2.466 g)

Workup

  1. customthen partitioned between water (100 ml) and ethyl acetate (3×50 ml)
  2. washThe combined organic extracts were washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-17dda0a9ef624123a04d0e4d23bd1049
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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