Diethyl Malonate → HCID 59395027, compound

HRID 383360Notes

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+].[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25](Br)=[CH:24][C:23]=1[CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CS(C)=O>[CH2:14]([O:21][C:22]1[C:23]([CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:24][C:25]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Diethyl malonate (1059 mg, 1.0 mL, 6.6 mmol) was added dropwise to a suspension of NaH (265 mg, 6.6 mmol) in DMSO (3.3 mL). The reaction mixture was warmed to 60° C. for 30 min. A solution of 1-benzyloxy-4-bromo-2-cyclopentyl-5-nitro-benzene (995 mg, 2.6 mmol) in DMSO (3 mL) was added dropwise and the reaction mixture heated at 100° C. for 2 h. The cooled solution was poured into ice water, and the aqueous layer extracted with dichloromethane (3×20 mL). The organic layer was dried down to an orange residue. Purification by silica gel chromatography (0-40% ethyl acetate/hexane) provided diethyl 2-(4-(benzyloxy)-5-cyclopentyl-2-nitrophenyl)malonate as a yellow oil (538 mg, 45% yield). LC/MS m/z 456.2 [M+H]+.

Workup

temperaturethe reaction mixture heated at 100° C. for 2 h
extractionthe aqueous layer extracted with dichloromethane (3×20 mL)
customThe organic layer was dried down to an orange residue
customPurification by silica gel chromatography (0-40% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-1fc7ae8fbedf4897a10f58639cf1d232
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367660B2

Reaction notes

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