Hydrochloric Acid → 3-(2-Methylbenzo[b]furan-5-yl)prop-2-yn-1-ol

HRID 1810641Notes

Reaction equation

HRID 1810641 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]2[O:6][C:7]([CH3:9])=[CH:8][C:4]=2[CH:3]=1.N12CCCN=C1CCCCC2.[CH2:23]([OH:26])[C:24]#[CH:25].Cl>O1CCCC1.[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.O>[CH3:9][C:7]1[O:6][C:5]2[CH:10]=[CH:11][C:2]([C:25]#[C:24][CH2:23][OH:26])=[CH:3][C:4]=2[CH:8]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 38560465-Iodo-2-methylbenzofuran

Product 1

HCID 671466183-(2-Methylbenzo[b]furan-5-yl)prop-2-yn-1-ol

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-iodo-2-methylbenzo[b]furan (12.1 g, 46.9 mmol) in dry tetrahydrofuran (50 mL) was degassed and copper(I)iodide (280 mg, 1.5 mmol), tetrakis(triphenylphosphine)palladium (1.7 g, 1.5 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (9.1 g, 60.0 mmol) were added. The reaction solution was degassed again and propargyl alcohol (3.4 g, 60.7 mmol) was added under inert atmosphere at ambient temperature. The reaction mixture was stirred (initially under cooling with ice water) for 48 h, then treated with water (20 mL) and acidified with 2 M hydrochloric acid (20 mL). The organic phase was separated and the aqueous phase was extracted with ether (4×30 mL). The combined organic phases were dried with anhydrous magnesium sulfate and concentrated in vacuo yielding brown solid. The residue was purified by column chromatography (silica gel Fluka 60, benzene) yielding 3-(2-methylbenzo[b]furan-5-yl)prop-2-yn-1-ol.

Workup

  1. customThe reaction solution was degassed again
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with ether (4×30 mL)
  4. dry with materialThe combined organic phases were dried with anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customyielding brown solid
  7. customThe residue was purified by column chromatography (silica gel Fluka 60, benzene)

Sources & evidence

ORD record
ord-cb5d5a3415be4a8d80db5b1ca7a7323a
Source dataset
uspto-grants-2013_01
Patent number
US08362016B2

Reaction notes

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