3-Butyn-1-OL → HCID 67402660, compound

HRID 906108Notes

Reaction equation

HRID 906108 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:14]([OH:18])[CH2:15][C:16]#[CH:17]>C(N(CC)CC)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>[OH:18][CH2:14][CH2:15][C:16]#[C:17][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 2

HCID 135663-Butyn-1-OLHCID 10922803methyl 2-bromo-3-methoxybenzoate

Product 1

HCID 67402660HCID 67402660, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of methyl 2-bromo-3-methoxybenzoate (0.4 g, 1.63 mmol), Pd(PPh3)2Cl2 (0.057 g, 0.082 mmol), copper (I) iodide (0.031 g, 0.16 mmol) and 3-butyn-1-ol (0.173 ml, 2.28 mmol) were stirred in trietylamine (5 ml) at 80° C. for 20 h. The solvent was concentrated under vacuum, and the residue was partitioned between ethyl acetate (15 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using hexanes:ethyl acetate 2:1 as eluent to afford methyl 2-(4-hydroxybut-1-yn-1-yl)-3-(methyloxy)benzoate (0.056 g; 15% yield). MS (EI) for C13H14O4: 235 (MH+).

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate (15 ml) and water (5 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e10546838e9f4573a9e9891932eb9656
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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