Diethyl [(3,4,5-trimethoxyphenyl)methylidene]propanedioate → HCID 12774292, compound

HRID 1074513Notes

Reaction equation

HRID 1074513 reaction equation
Br[C:2]1[C:7]([CH2:8]Cl)=[CH:6][C:5]2[O:10][CH2:11][O:12][C:4]=2[CH:3]=1.C([Li])(C)(C)C.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:30]=[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27]>>[C:37]([C:31]1([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:8][C:7]2[C:2](=[CH:3][C:4]3[O:12][CH2:11][O:10][C:5]=3[CH:6]=2)[CH:30]1[C:22]1[CH:21]=[C:20]([O:19][CH3:18])[C:25]([O:26][CH3:27])=[C:24]([O:28][CH3:29])[CH:23]=1)([O:39][CH2:40][CH3:41])=[O:38]

Participants

4

Reactant 3

HCID 349318Diethyl [(3,4,5-trimethoxyphenyl)methylidene]propanedioateHCID 24465455-Bromo-6-(chloromethyl)-2H-1,3-benzodioxoleHCID 178418306HCID 178418306, compound

Product 1

HCID 12774292HCID 12774292, compoundYield 81%

Procedure

6-bromo-3,4-methylenedioxybenzyl chloride (364 mg, 1.45 mmol) is reacted as in Example 2 with t-butyllithium (0.98 ml, 1.5 mmol, 1.55 M in pentane) and diethyl (3,4,5-trimethoxyphenyl)methylenemalonate (490 mg, 1.45 mmol) to provide the title compound (551 mg, 81% yield).

Sources & evidence

ORD record
ord-1a7cf98f23a24decb0e22f03bc0550ad
Source dataset
uspto-grants-1983_07
Patent number
US04391982

Reaction notes

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