Maltol → HCID 54767214, compound

HRID 336120Notes

Reaction equation

HRID 336120 reaction equation
[CH3:1][C:2]1[O:8][CH:7]=[CH:6][C:4](=[O:5])[C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([B:24]2[O:32][C:29]([CH3:31])([CH3:30])[C:26]([CH3:28])([CH3:27])[O:25]2)=[CH:20][CH:19]=1>C(#N)C>[CH3:1][C:2]1[O:8][CH:7]=[CH:6][C:4](=[O:5])[C:3]=1[O:9][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([B:24]2[O:25][C:26]([CH3:28])([CH3:27])[C:29]([CH3:31])([CH3:30])[O:32]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8369MaltolHCID 11430Potassium CarbonateHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 54767214HCID 54767214, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Maltol (0.50 g, 3.96 mmol) was dissolved in 25 mL of acetonitrile followed by the addition of 1.6 g (11.88 mmol) of K2CO3. The reaction was heated to reflux for 10 min before adding 4-bromomethylphenyl boronic acid pinacol ester (1.3 g, 4.4 mmol). The reaction was left stirring under refluxing conditions for 12 h then cooled to room temperature and filtered rinsing with DCM. The resulting filtrate was concentrated and purified via silica gel chromatography eluting with 0-2% MeOH in DCM. B20 (1.03 g, 3.0 mmol) was collected and dried yielding a pale yellow solid in 76% yield. 1H NMR (400 MHz, CDCl3) δ=7.77 (d, J=7.6 Hz, 2H), 7.58 (d, J=5.2 Hz, 1H), 7.37 (d, J=7.6 Hz, 2H), 6.35 (d, J=5.6 Hz, 1H), 5.19 (s, 2H), 2.06 (s, 3H), 1.34 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=175.3, 160.0, 153.6, 143.9, 140.0, 135.1, 128.5, 117.4, 84.1, 73.6, 25.1, 15.2. ESI-MS(+): m/z 343.18 [M+H]+. Anal. calcd. for C19H23BO5: C, 66.69; H, 6.77. Found: C, 66.34; H, 6.67.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 10 min
  3. waitThe reaction was left
  4. filtrationfiltered
  5. washrinsing with DCM
  6. concentrationThe resulting filtrate was concentrated
  7. custompurified via silica gel chromatography
  8. washeluting with 0-2% MeOH in DCM
  9. customB20 (1.03 g, 3.0 mmol) was collected
  10. customdried
  11. customyielding a pale yellow solid in 76% yield

Sources & evidence

ORD record
ord-4e327231f3de4866b154397520dffe15
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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