Propargyl alcohol → Methyl 2-(3-hydroxyprop-1-yn-1-yl)benzoate

HRID 368855Notes

Reaction equation

HRID 368855 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].[CH2:12]([OH:15])[C:13]#[CH:14]>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)I.C(NCC)C>[OH:15][CH2:12][C:13]#[C:14][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 7859Propargyl alcoholHCID 69132Benzoic acid, 2-iodo-, methyl ester

Product 1

HCID 4321316Methyl 2-(3-hydroxyprop-1-yn-1-yl)benzoate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

Step 1--A mixture of methyl o-iodobenzoate (9.17 g), propargyl alcohol (3.06 ml) and diethyl amine (90 ml) is treated with bis(triphenylphosphine)palladium chloride (1.23 g) and copper iodide (333 mg) and the reaction is stirred at 20-25° under nitrogen for 18 hrs. The reaction is then filtered through a filter agent and concentrated. The resulting residue is partitioned between water and dichloromethane. The combined organic phases are washed once with saline, dried over magnesium sulfate, filtered and concentrated to an oil. Purification by silica gel chromatography gives methyl o-(1-hydroxy-2-propyn-3-yl)benzoate (CXIX).

Workup

  1. filtrationThe reaction is then filtered through a filter agent
  2. concentrationconcentrated
  3. customThe resulting residue is partitioned between water and dichloromethane
  4. washThe combined organic phases are washed once with saline
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-0e61106d4fea4f3baccde1a66c956168
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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