Hydrochloric Acid → HCID 68109356, compound

HRID 1429281Notes

Reaction equation

HRID 1429281 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[CH2:13]([OH:16])[C:14]#[CH:15].C(NC(C)C)(C)C.Cl>CN(C=O)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.O.C(OCC)(=O)C>[OH:16][CH2:13][C:14]#[C:15][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 7912DiisopropylamineHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 68109356HCID 68109356, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

9.00 g (40.3 mmol) of 6-bromonaphthalen-2-ol, 3.5 g (62.4 mmol) of prop-2-yn-1-ol, 1.00 g (1.43 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.5 g (2.63 mmol) of copper(I) iodide and 10 ml of diisopropylamine are left to stir overnight at 80° C. in 60 ml of DMF. The batch is subsequently added to 200 ml of ethyl acetate, 400 ml of water are added, and the mixture is acidified using hydrochloric acid. The aqueous phase is separated off and extracted three times with ethyl acetate. The combined org. phases are evaporated in vacuo, and the residue is filtered through silica gel with toluene/ethyl acetate (2:1). Crystallisation of the crude product from toluene/heptane gives 6-(3-hydroxyprop-1-ynyl)naphthalen-2-ol as a colourless solid.

Workup

  1. additionare added
  2. customThe aqueous phase is separated off
  3. extractionextracted three times with ethyl acetate
  4. customphases are evaporated in vacuo
  5. filtrationthe residue is filtered through silica gel with toluene/ethyl acetate (2:1)
  6. customCrystallisation of the crude product from toluene/heptane

Sources & evidence

ORD record
ord-42e236eea22c4664b6c01be09988e97e
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

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