3,4-Bis-(1,1-dimethyl-prop-2-ynyloxy)-xanthen-9-one → 3,4-Bis-(1,1-dimethyl-allyloxy)-xanthen-9-one

HRID 734185Notes

Reaction equation

HRID 734185 reaction equation
[CH3:1][C:2]([CH3:27])([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[O:26])[C:11]3[C:16]([O:17][C:18]=2[C:19]=1[O:20][C:21]([CH3:25])([CH3:24])[C:22]#[CH:23])=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:3]#[CH:4]>CO.[Pd]>[CH3:1][C:2]([CH3:27])([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[O:26])[C:11]3[C:16]([O:17][C:18]=2[C:19]=1[O:20][C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=[CH2:4]

Participants

4

Reactant 1

HCID 593560783,4-Bis-(1,1-dimethyl-prop-2-ynyloxy)-xanthen-9-one

Product 1

HCID 161050363,4-Bis-(1,1-dimethyl-allyloxy)-xanthen-9-oneYield 77.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3,4-bis-(1,1-dimethyl-prop-2-ynyloxy)-xanthen-9-one (318 mg, 0.882 mmol) in methanol (25 mL) was added Lindlar's catalsyt (Pd, 5 wt % on calcium carbonate, 75 mg) under hydrogen (1 atm). The mixture was stirred at room temperature for 1 h, then the mixture was filtered through a syringe filter and the solvent was evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-25%) to give the product as a white solid (249 mg, 77%): 1H NMR (CDCl3,300 MHz) δ 8.31 (dd, J=1.8, 8.1 Hz, 1H), 7.93 (d, J=9.0 Hz, 1H), 7.70 (m, 1H), 7.50 (dd, J=0.9, 8.7 Hz, 1H), 7.37 (m, 1H), 7.13 (d, J=9.0 Hz, 1H), 6.30 (dd, J=10.8, 17.7 Hz, 1H), 6.20 (dd, J=11.1, 17.1 Hz, 1H), 5.25-5.16 (m, 3H), 5.03 (dd, J=0.9, 10.5 Hz, 1H), 1.59 (s, 3H), 1.58 (s, 3H).

Workup

  1. filtrationthe mixture was filtered through a syringe
  2. filtrationfilter
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-25%)

Sources & evidence

ORD record
ord-a96cab07baf74707b06308eaea1f575d
Source dataset
uspto-grants-2009_09
Patent number
US07592143B2

Reaction notes

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