Pyrogallol → HCID 11630083, compound

HRID 1844294Notes

Reaction equation

HRID 1844294 reaction equation
[OH:1][C:2]1[C:3](O)=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:10](Br)[C:11]#[CH:12].[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH2:20]1OCCOCCOCCOCCOCCO[CH2:21]1.[CH2:38]1[CH2:42]OC[CH2:39]1>>[CH2:10]([O:8][C:4]1[CH:5]=[C:6]([O:17][CH2:14][C:20]#[CH:21])[CH:7]=[C:2]([O:1][CH2:39][C:38]#[CH:42])[CH:3]=1)[C:11]#[CH:12]

Participants

6

Reactant 5

HCID 1057PyrogallolHCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2855718-Crown-6

Product 1

HCID 11630083HCID 11630083, compoundYield 72%

Procedure

Trihydroxybenzene (0.5 g 3.08 mmol) and propargyl bromide (4 ml, 12 mmol) were dissolved in 10 mL THF, dry potassium carbonate (3.75 g, 12 mmol) and catalytic amount 18-crown-6-ether was added. The reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated and the mixture was dissolved in DCM, washed with brine. Concentration afforded crude product which was further purified by silica gel chromatography (1:2 ethyl acetate:hexane), giving compounds 17 0.54 g (72%). TLC (1:2 ethyl acetate:hexane): Rf=0.36. 1H NMR (400 MHz, CDCl3) δ 6.26 (3H, s), 4.64 (6H, d, J=2.4 Hz), 2.54 (3H, t, J=2.4 Hz). 13C NMR (100 MHz, CDCl3) δ 159.41, 95.50, 78.35, 75.88, 56.04. Low-resolution mass spectrum (ESI) calcd. for C15H13O3 [M+H]+: 241.08. Found: 241.00.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe mixture was dissolved in DCM
  3. washwashed with brine
  4. concentrationConcentration
  5. customafforded crude product which
  6. customwas further purified by silica gel chromatography (1:2 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-073a2f9019c3401e952f9d03f46ef5ac
Source dataset
uspto-grants-2015_02
Patent number
US08946391B2

Reaction notes

Loading…