Tetrahydrofuran → Phenyl-t-butylacetylene

HRID 2295966

Reaction equation

[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=CC=C[CH:2]=1.O1CCC[CH2:16]1>>[C:9]1([C:8]#[C:7][C:1]([CH3:2])([CH3:6])[CH3:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 8028Tetrahydrofuran

HCID 10390Diphenylacetylene

Product 1

HCID 138165Phenyl-t-butylacetyleneYield 100%

Conditions

Temperature: 60 °C

Procedure

A solution containing W(CCMe3)(Cl3)(OPEt3) (0.43 g, 0.866 mmol) and diphenylacetylene (0.18 g, 1.0 mmol) in 2 ml of tetrahydrofuran was heated to 60° C. for 2 hours. During this time, the color of the reaction mixture changed from blue to green. Phenyl-t-butylacetylene (100% yield versus tungsten) was observed in the reaction mixture by gas chromatography. The reaction mixture was filtered and PMe3 (0.30 ml, 3.0 mmol) was added by syringe. The color of the solution turned yellow, and after the addition of 2 ml pentane, yellow crystals precipitated from solution. The product was collected by filtration and was recrystallized from a mixture of tetrahydrofuran and pentane at -30° C.; total yield 0.47 g (89%) W(CPh)Cl3 (PMe3)3.

Sources & evidence

ORD record: ord-c9c69b858aa74e3bbc0899fa50a565cd
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04427595

Linked notes

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