1-p-Tolyl-hex-5-en-1-yn-3-ol → 1-p-Tolyl-bicyclo[3.1.0]hexan-3-one

HRID 1096698Notes

Reaction equation

[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]#[C:8][CH:9]([OH:13])[CH2:10][CH:11]=[CH2:12])=[CH:3][CH:2]=1>C1(C)C=CC=CC=1>[C:1]1([CH3:14])[CH:2]=[CH:3][C:4]([C:7]23[CH2:12][CH:11]2[CH2:10][C:9](=[O:13])[CH2:8]3)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

PtCl2 (157 mg; 5 mol %) was added to a solution of 1-p-tolyl-hex-5-en-1-yn-3-ol (2.20 g; 11.8 mmol) in toluene (60 mL) and the resulting mixture was stirred at 80° C. for 24 h until the reaction was complete as shown by TLC. The toluene was concentrated at 45-50° C. using a rotary evaporator, and the residue was purified by flash chromatography (9:1→3:1 heptane/EtOAc) to give the desired product (880 mg; 40%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.68 (t, 1 H) 1.26-1.30 (m, 1 H) 1.92-1.97 (m, 1 H) 2.33 (s, 3 H) 2.39 (d, 1 H) 2.60-2.65 (d, 1H) 2.75-2.86 (m, 1 H) 2.88-2.93 (m, 1H) 7.07-7.14 (m, 4H).

Workup

concentrationThe toluene was concentrated at 45-50° C.
customa rotary evaporator
customthe residue was purified by flash chromatography (9:1→3:1 heptane/EtOAc)

Sources & evidence

ORD record: ord-5c8cc19facc8430b85d022362bf384b6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138377B2

Reaction notes

Loading…