HCID 13007670, compound → HCID 13007671, compound

HRID 990318Notes

Reaction equation

HRID 990318 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[C:10][CH:11]([OH:20])[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]#[C:10][C:11](=[O:20])[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 13007670HCID 13007670, compound

Product 1

HCID 13007671HCID 13007671, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

C19H14O, FW=258.31 g/mol. 1-(2,6-Dimethylphenyl)-5-phenyl-1,4-pentadiyn-3-ol (1.57 g, 6.03 mmol) and manganese dioxide (3.15 g, 36.2 mmol) were combined in dichloromethane (35 mL) and stirred at room temperature for 40 minutes. Following completion of the reaction, the reaction mixture is filtered through celite, concentrated and the orange liquid product is isolated in 93% yield. Rf 0.90 (DCM) 1H NMR (500 MHz, CDCl3, ppm) d 7.61 (d, 2H, J=7.3 Hz), 7.48 (t, 1H, J=7.6 Hz), 7.40 (Ar, m, 3H), 7.08 (d, 2H, J=7.6 Hz), 2.52 (s, 6H); 13C NMR (125 MHz, CDCl3, ppm) d 160.7, 143.2, 133.3, 131.2, 131.0, 128.8, 127.2, 119.6, 119.3, 97.8, 91.5, 90.6, 89.6, 20.9; HR MS (EI) m/z calculated. 258.104465, found 258.104127.

Workup

  1. customcompletion of the reaction
  2. filtrationthe reaction mixture is filtered through celite,
  3. concentrationconcentrated
  4. customthe orange liquid product is isolated in 93% yield

Sources & evidence

ORD record
ord-b163354084eb4e7c8b8ab9fc54daeab2
Source dataset
uspto-grants-2002_10
Patent number
US06458967B1

Reaction notes

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