Dimethyl malonate → Dimethyl 2,2-di[4-(diethoxymethyl)benzyl]malonate

HRID 566502Notes

Reaction equation

[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:14][CH:13]=1.[H-].[Na+]>CN(C=O)C>[CH2:20]([O:19][CH:18]([O:22][CH2:23][CH3:24])[C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:2]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24])=[CH:16][CH:17]=2)([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:14]=1)[CH3:21]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of dimethyl malonate (0.66 g), 1-(bromomethyl)-4-(diethoxymethyl)benzene (2.73 g) in DMF (30 mL) was treated with NaH (0.4 g, 60% in mineral oil). The mixture was stirred for 3 h at room temperature and 1 h at 50° C., and then quenched with 100 mL of saturated NH4Cl. The product was extracted with 200 mL of 1:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated to give the title compound (3 g) which was used without further purification.

Workup

customquenched with 100 mL of saturated NH4Cl
extractionThe product was extracted with 200 mL of 1:1 hexane/EtOAc
dry with materialThe extract was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-7f01272e155446ad8f83b6e11d8d320d
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174874B1

Reaction notes

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