1-Naphthalen-1-yl-hex-5-en-1-yn-3-ol → 1-Naphthalen-1-yl-bicyclo[3.1.0]hexan-3-one

HRID 1096727Notes

Reaction equation

[C:1]1([C:11]#[C:12][CH:13]([OH:17])[CH2:14][CH:15]=[CH2:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1.[Pt](Cl)Cl>[C:1]1([C:11]23[CH2:16][CH:15]2[CH2:14][C:13](=[O:17])[CH2:12]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 1-naphthalen-1-yl-hex-5-en-1-yn-3-ol (1.00 g, 4.50 mmol) under an atmosphere of nitrogen in toluene (100 mL) was added platinum chloride (0.06 g, 0.22 mmol, 5 mol %); the resulting black mixture was stirred at 80° C. for 24 hr. TLC indicated that the reaction was complete. The organics were concentrated in vacuo to afford a black residue. The crude material was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 10%:90%) to afford the desired compound as a yellow oil (0.57 g, 57%). 1H NMR (400 MHz, CDCl3) δ ppm 0.73 (1H, t, J 4.0 Hz, CH), 0.82-0.84 (1H, m, CH), 1.17-1.24 (1H, m, CH), 2.47 (1H, d, J 19.0 Hz, CH), 2.75 (2H, d, J 10 Hz, CH)), 2.95-3.09 (1H, m, CH), 7.38-7.51 (4H, m, ArH), 7.73 (1H, d, J 8.0 Hz, ArH), 7.84 (1H, d, J 8.0 Hz, ArH), 8.10 (1H, d, J 8.0 Hz, ArH).

Workup

concentrationThe organics were concentrated in vacuo
customto afford a black residue
customThe crude material was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 10%:90%)

Sources & evidence

ORD record: ord-1b6aaf6e8b864e599722e7f281cdb954
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138377B2

Reaction notes

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