3-Butyn-2-ol → HCID 11816547, compound

HRID 634345Notes

Reaction equation

HRID 634345 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:12][CH:13]([OH:16])[C:14]#[CH:15]>CN(C=O)C.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.[Cu]I>[OH:16][CH:13]([CH3:12])[C:14]#[C:15][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 2

HCID 162393-Butyn-2-olHCID 69132Benzoic acid, 2-iodo-, methyl ester

Product 1

HCID 11816547HCID 11816547, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
60 °C

Procedure

Pd(PPh3)4 (1.9 g, 0.006 eq) and CuI (2.6 g, 0.05 eq) were suspended in DMF (350 ml). Methyl 2-iodobenzoate (70.8 g, 1 eq), but-3-yn-2-ol (32 ml, 1.5 eq), TEA (75 ml, 2 eq) were added under nitrogen atmosphere and the mixture was stirred at 60° C. for 6 hrs and at RT. overnight. The precipitated solid was filtered off, the mother liquors was diluted with a saturated solution of NaClaqueous and extracted with EtOAc (twice). The collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound, as a brownish thick oil (47.7 g).

Workup

  1. customovernight
  2. filtrationThe precipitated solid was filtered off
  3. additionthe mother liquors was diluted with a saturated solution of NaClaqueous
  4. extractionextracted with EtOAc (twice)
  5. dry with materialThe collected organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da96d5edd40b4e7b93853eb445c2ef31
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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