1-Naphthol → HCID 44220679, compound

HRID 868834Notes

Reaction equation

HRID 868834 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:12][CH:13](O)[C:14]#[CH:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl.O>[CH3:15][CH:14]([O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:13]#[CH:12]

Participants

7

Reactant 4

HCID 70051-NaphtholHCID 11776TriphenylphosphineHCID 162393-Butyn-2-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 44220679HCID 44220679, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-naphthol (200 mg, 1.38 mmol) and but-3-yn-2-ol (146 mg, 2.07 mmol) in anhydrous DCM (10 mL) under a N2 atmosphere and at 0° C. was added Ph3P (435 mg, 1.66 mmol) portion wise. The reaction mixture was stirred for 10 min and then DEAD (360 mg, 2.07 mmol) (70% solution in toluene) was slowly added. The resulting reaction solution was stirred at the room temperature for 24 h and then diluted with water (50 mL) and extracted with chloroform (3×50 mL). The combined organic extracts were washed with brine, dried over anhydrous MgSO4, filtered concentrated in vacuo and the residue was purified by flash column chromatography using ethyl acetate/n-hexane (a gradient of 5-10%) to furnish 1-[(1-methyl-2-propyn-1-yl)oxy]naphthalene (176 mg, 65%) as a viscous oil.

Workup

  1. customThe resulting reaction solution
  2. stirringwas stirred at the room temperature for 24 h
  3. extractionextracted with chloroform (3×50 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-affed02756af4a5394817745ffe08e49
Source dataset
uspto-grants-2015_03
Patent number
US08969342B2

Reaction notes

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