Dimethylformamide → Methyl 2-(hex-1-yn-1-yl)benzoate

HRID 1992928Notes

Reaction equation

HRID 1992928 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[CH:11]#[C:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:17]N(C=O)C>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>[C:11]([C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5])#[C:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 127321-HexyneHCID 4739928Benzoic acid, 2-iodo-, ion(1-)

Product 1

HCID 11333401Methyl 2-(hex-1-yn-1-yl)benzoateYield 90%

Reagents, catalysts & solvents 2

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

Procedure

Coupling of 2-iodobenzoate (3.0 g, 11.5 mmol) with 1-hexyne (2.71 mL, 22.9 mmol) using Pd(PPh3)2Cl2 and CuI in DMF at room temperature gave 2.23 g (90%) of compound 157 as a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.95 (t, J=7.3 Hz, 3H), 1.45-1.55 (m, 2H), 1.55-1.65 (m, 2H), 2.47 (t, J=7.0 Hz, 2H), 3.91 (s, 3H), 7.26-7.33 (m, 1H), 7.37-7.44 (m, 1H), 7.50 (d, J=7.7 Hz, 1H), 7.87 (d, J=7.9 Hz, 1H). LCMS (APCI): m/z 217 (M+H)+.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-fd38002cbe2b49cb9980a0817842f9d7
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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