HCID 59779169, compound → HCID 59779133, compound

HRID 1096737Notes

Reaction equation

HRID 1096737 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[C:12][CH:13]([OH:17])[CH2:14][CH:15]=[CH2:16]>C1(C)C=CC=CC=1.[Pt](Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]12[CH2:16][CH:15]1[CH2:14][C:13](=[O:17])[CH2:12]2

Participants

4

Reactant 1

HCID 59779169HCID 59779169, compound

Product 1

HCID 59779133HCID 59779133, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 2770Platinous chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-naphthalen-2-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 (0.64 g, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 0.70 (1H, t, J 4.0 Hz, CH), 0.83-0.86 (1H, m, CH), 1.41-1.44 (1H, m, CH), 2.44 (1H, d, J 18.0 Hz, CH), 2.75 (1H, d, J 18 Hz, CH2), 2.86-2.91 (1H, m, CH), 3.05 (1H, d, J 18.0 Hz, CH), 7.24-7.26 (1H, m, ArH), 7.44-7.49 (2H, m, ArH), 7.63 (1H, s, ArH), 7.80 (1H, d, J 8.0 Hz, ArH).

Workup

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

Sources & evidence

ORD record
ord-8b861f06a661441c8e38c2c6ecb29919
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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