Sodium hydride → Diethyl 2-(4-benzyloxybenzyl)-2-(4-isopropylphenoxy)malonate

HRID 1859963

Reaction equation

[CH:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:22]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[H-].[Na+]>>[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:34][C:9]([O:8][C:7]2[CH:20]=[CH:21][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][CH:6]=2)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:36][CH:37]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 700424-Benzyloxybenzyl chloride

HCID 10565722Diethyl 2-(4-isopropylphenoxy)malonate

Product 1

HCID 18625725Diethyl 2-(4-benzyloxybenzyl)-2-(4-isopropylphenoxy)malonateYield 90.1%

Procedure

In a similar manner to that described in Reference example 2(a), a reaction was carried out using diethyl 2-(4-isopropylphenoxy)malonate (21.5 g), which is the product of Reference example 5(a), 4-benzyloxybenzyl chloride (19.7 g) and sodium hydride (55% suspension in oil, 3.53 g) and the reaction mixture was treated to afford the desired compound (32.3 g) as a syrup.

Workup

additionthe reaction mixture was treated

Sources & evidence

ORD record: ord-46561211f63848708c303895625923ff
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528525B1

Linked notes

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