1-Pentyne → Methyl 2-(pent-1-ynyl)benzoate

HRID 634401Notes

Reaction equation

HRID 634401 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH3:5].I[C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]>CN(C=O)C.CCN(CC)CC.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])#[C:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 2

HCID 123091-PentyneHCID 69132Benzoic acid, 2-iodo-, methyl ester

Product 1

HCID 10352815Methyl 2-(pent-1-ynyl)benzoateYield 101%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Pent-1-yne (5.6 mL, 57.2 mmol) was added to methyl 2-iodobenzoate (5.6 mL, 38.2 mmol), copper(I) iodide (1.0 g, 5.72 mmol) and Pd(PPh3)4 (1.3 g, 1.14 mmol) in DMF (5 mL) and Et3N (1 mL) at RT for 3 hrs. The reaction was partitioned between Et2O and 0.1 M HClaqueous. The resulting organic phase was washed with 0.1 M HClaqueous, NaHCO3aqueous and brine. Organic phase was then anhydrified over Na2SO4 and dried under reduced pressure to give methyl 2-(pent-1-ynyl)benzoate (7.8 g) as a dark oil. The crude will be used in the next step without further purification.

Workup

  1. customThe reaction was partitioned between Et2O and 0.1 M HClaqueous
  2. washThe resulting organic phase was washed with 0.1 M HClaqueous
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-4055372eb29b4f4db33ed8f453113ef9
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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