Triphenylphosphine → (But-3-yn-2-yloxy) Benzene

HRID 64243

Reaction equation

HRID 64243 reaction equation
C([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)C(O)(C)C)(=O)C.[CH3:14][CH:15]([OH:18])[C:16]#[CH:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH3:14][CH:15]([O:18][C:4]1[CH:5]=[CH:6][CH:11]=[CH:12][CH:13]=1)[C:16]#[CH:17]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 162393-Butyn-2-olHCID 5462977Diethyl azodicarboxylateHCID 135314191-(3-(1-Hydroxy-1-methylethyl)phenyl)ethanone

Product 1

HCID 12519596(But-3-yn-2-yloxy) Benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phenol 27 (422.9 mg, 4.49 mmol), But-3-yn-2-ol (300 mg, 4.28 mmol) were dissolved in anhydrous THF (10 mL) under N2 atmosphere, at 0° C. was added Ph3P (1.12 g, 4.26 mmol) portion wise, stirred it for 10 min, and then DEAD (894.6 mg, 5.14 mmol) added slowly. The resultant solution was heated up to 70° C. stirred for 20 h. To the reaction mixture water added and extracted with DCM and dried organic layer on MgSO4, filtered, concentrated. Purified by flash chromatography using ethylacetate/n-hexane, 5:95) provided compound 28 (450 mg, 69%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 1.67 (d, J=6.8 Hz, 3H), 2.47 (d, J=2 Hz, 1H), 4.88 (q, J=2 Hz, 1H), 6.97-7.03 (m, 3H), 7.28-7.32 (m, 2H).

Workup

  1. stirringstirred for 20 h
  2. extractionextracted with DCM and dried organic layer on MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurified by flash chromatography
  6. customprovided compound 28 (450 mg, 69%) as a solid

Sources & evidence

ORD record
ord-c87323b5de76448da663a06fe061e6df
Source dataset
uspto-grants-2016_09
Patent number
US09447134B2

Linked notes

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