(1,1'-Biphenyl)-2-ol → 2-(Prop-2-yn-1-yloxy)-1,1'-biphenyl

HRID 567668Notes

Reaction equation

[CH2:1](Br)[C:2]#[CH:3].[C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:3][C:2]#[CH:1])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of propargyl bromide (80% solution in toluene, 500 δ 3.36 mmol) in acetone (15 ml) at 23° C. was added 2-phenyl phenol (316 mg, 1.86 mmol) and potassium carbonate (1.05 g, 7.61 mmol). After being stirred in a sealed reaction vial at 65° C. for 14 hours, the reaction was concentrated in vacuo, the residue purified by flash chromatography (ethyl acetate:hexane: 9:1) to afford compound 5 in 95% yield. 1H NMR(CDCl3) δ 2.45-2.55 (m, 1H), 4.60-4.70 (m, 2H), 6.99-7.43 (m, 9H).

Workup

concentrationthe reaction was concentrated in vacuo
customthe residue purified by flash chromatography (ethyl acetate:hexane: 9:1)

Sources & evidence

ORD record: ord-41e3eda5c1da40ad92c79519a5855b5f
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180615B2

Reaction notes

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