HCID 10104617, compound → HCID 10330756, compound

HRID 990319Notes

Reaction equation

HRID 990319 reaction equation
[CH3:1][C:2]([C:5]#[C:6][CH:7]([OH:16])[C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])[CH3:3]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:4][C:2]([C:5]#[C:6][C:7](=[O:16])[C:8]#[C:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 10104617HCID 10104617, compound

Product 1

HCID 10330756HCID 10330756, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(C15H14O), FW=210.27 g/mol. 1-(1,1-dimethylethyl)-5-phenyl-1,4-pentadiyn-3-ol (5.46 g, 25.6 mmol) was dissolved in dichloromethane (134 mL). Manganese dioxide (13.42 g, 154 mmol) was added and the reaction was heated to reflux for 45 minutes. The reaction mixture was cooled and filtered through celite and concentrated. The orange liquid was obtained in 95% yield. Rf 0.72 (DCM) 1H NMR (500 MHz, CDCl3, ppm) d 7.59 (d, 2H, J=7.3 Hz), 7.46 (t, 1H, J=7.3 Hz), 7.38 (t, 2H, J=7.3 Hz) 1.32 (s, 9H); 13C NMR (75 MHz, CDCl3, ppm) d 161.3, 133.2, 131.0, 128.6, 119.6, 102.6, 90.3, 89.4, 80.8, 29.8, 27.9; HRMS(EI) m/z calculated 210.104465, found 210.103678.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 45 minutes
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationconcentrated
  6. customThe orange liquid was obtained in 95% yield

Sources & evidence

ORD record
ord-283eb94f4d8d48048adc303d1612fc61
Source dataset
uspto-grants-2002_10
Patent number
US06458967B1

Reaction notes

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