Pinacol → HCID 78265135, compound

HRID 634419Notes

Reaction equation

HRID 634419 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1)=[O:2].[CH3:12][C:13]([OH:19])([C:15]([CH3:18])(O)[CH3:16])[CH3:14]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:12][C:13]1([CH3:14])[C:15]([CH3:18])([CH3:16])[O:11][B:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH:1]3[O:19][C:13]([CH3:14])([CH3:12])[C:15]([CH3:18])([CH3:16])[O:2]3)[CH:4]=2)[O:10]1

Participants

5

Reactant 2

HCID 6425PinacolHCID 27343563-Formylphenylboronic acid

Product 1

HCID 78265135HCID 78265135, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

(3-formylphenyl)boronic acid (5 g, 33.3 mmol), 2,3-dimethylbutane-2,3-diol (19.70 g, 167 mmol) and p-toluensulfonic acid monohydrate (0.317 g, 1.667 mmol) were dissolved in toluene (278 mL) and refluxed with a Dean-Stark equipment for 3 h until reaction completion. The mixture was dried under reduced pressure and the residue diluted with AcOEt (250 mL) and washed three times with abundant water, once with saturated NaClaqueous (250 mL), anhydrified over Na2SO4 and the solvent removed under reduced pressure. The crude was purified via flash chromatography on silica gel using a Biotage 100G+50G SNAP with a gradient of hexane and AcOEt to give the title compound (8.5 g, 77%) as white solid.

Workup

  1. temperaturerefluxed with a Dean-Stark equipment for 3 h until reaction completion
  2. customThe mixture was dried under reduced pressure
  3. additionthe residue diluted with AcOEt (250 mL)
  4. washwashed three times with abundant water
  5. customonce with saturated NaClaqueous (250 mL), anhydrified over Na2SO4 and the solvent removed under reduced pressure
  6. customThe crude was purified via flash chromatography on silica gel using a Biotage 100G+50G SNAP with a gradient of hexane and AcOEt

Sources & evidence

ORD record
ord-6da6d1244808423fa00169c869df0568
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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