1-(3,4-Dichlorophenyl)hex-5-en-1-yn-3-ol → 1-(3,4-Dichlorophenyl)bicyclo[3.1.0]hexan-3-one

HRID 1096712Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH:11]([OH:15])[CH2:12][CH:13]=[CH2:14])[CH:5]=[CH:6][C:7]=1[Cl:8]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:14][CH:13]2[CH2:12][C:11](=[O:15])[CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

PtCl2 (5 mol %) was added to a solution of 1-(3,4-dichlorophenyl)hex-5-en-1-yn-3-ol (2.98 g; 12.36 mmol) in toluene (65 mL) and the resulting mixture was stirred at 80° C. for 30 h until the reaction was complete by TLC. The toluene was concentrated at 45-50° C. using a rotary evaporator, and the residue was purified by flash chromatography (9:1→2:1 heptane/EtOAc) to give the desired product (895 mg; 30%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.68 (t, 1 H) 1.25-1.30 (m, 1 H) 1.90-1.99 (m, 1 H) 2.36-2.41 (d, 1 H) 2.59-2.64 (d, 1 H) 2.80-2.89 (m, 2 H) 7.00 (d, 1H) 7.25 (s, 1H) 7.37 (d, 1 H).

Workup

concentrationThe toluene was concentrated at 45-50° C.
customa rotary evaporator
customthe residue was purified by flash chromatography (9:1→2:1 heptane/EtOAc)

Sources & evidence

ORD record: ord-47e3e78ee8584ea888222fdad8dc95bf
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138377B2

Reaction notes

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