Methyl 4-pentynoate → HCID 58481154, compound

HRID 1625702Notes

Reaction equation

HRID 1625702 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([O:19][CH3:20])(=[O:18])[CH2:14][CH2:15][C:16]#[CH:17]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:17]#[C:16][CH2:15][CH2:14][C:13]([O:19][CH3:20])=[O:18])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11])=[O:7]

Participants

5

Reactant 2

HCID 543061Methyl 4-pentynoateHCID 6080994-Bromo-2-nitrobenzaldehyde

Product 1

HCID 58481154HCID 58481154, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

A mixture of 4-bromo-2-nitrobenzaldehyde (460 mg), Pd(PPh3)2Cl2 (70 mg), and CuI (38 mg), methyl pent-4-ynoate (269 mg) in TEA(5.0 mL) was stirred at room temperature until the reaction was completed. The crude residue was purified by a silica gel flash chromatography (15% EtOAc in hexanes), affording methyl 5-(4-formyl-3-nitrophenyl)pent-4-ynoate. ESI-MS m/z 262.23 (MH+).

Workup

  1. customThe crude residue was purified by a silica gel flash chromatography (15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-63db8492dd324d418d45b869fffe641a
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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