6-(Benzyloxy)benzo[c][1,2]oxaborol-1(3H)-ol → 1,3-Dihydro-2,1-benzoxaborole-1,6-diol

HRID 529194Notes

Reaction equation

HRID 529194 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:12]2[CH2:13][O:14][B:15]([OH:16])[C:11]=2[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[CH:18]=[CH:17][C:12]2[CH2:13][O:14][B:15]([OH:16])[C:11]=2[CH:10]=1

Participants

5

Reactant 2

HCID 529192896-(Benzyloxy)benzo[c][1,2]oxaborol-1(3H)-olHCID 178418361HCID 178418361, compound

Product 1

HCID 529192911,3-Dihydro-2,1-benzoxaborole-1,6-diolYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

H178 (13 mmol) was dissolved in MeOH (300 mL). To this solution under nitrogen was added 10% Pd/C (200 mg). The reaction mixture was vacuumed and backfilled hydrogen for 3 times, then stirred overnight at room temperature. After filtration and rotary evaporation, the residue was purified by recrystallization to give H181 (1.98 mg, 98% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.29 (s, 1H), 9.04 (s, 1H), 7.18 (d, J=8.4 Hz, 2H), 6.87 (dd, J=8.1 & 2.4 Hz, 1H) and 4.86 (s, 2H) ppm. Mp 133-135° C.

Workup

  1. filtrationAfter filtration and rotary evaporation
  2. customthe residue was purified by recrystallization
  3. customto give H181 (1.98 mg, 98% yield)

Sources & evidence

ORD record
ord-27468fa9debe4e5fb1b943adac655803
Source dataset
uspto-grants-2016_05
Patent number
US09346834B2

Reaction notes

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