Hydrochloric Acid → 1-(1-Hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethanone

HRID 1037043Notes

Reaction equation

HRID 1037043 reaction equation
C(OCOC([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[B:18]1[O:22]C(C)(C)[C:20]([CH3:26])([CH3:25])[O:19]1)(C)C)C.Cl.O>C1COCC1>[OH:22][B:18]1[C:10]2[CH:11]=[C:12]([C:15](=[O:17])[CH3:16])[CH:13]=[CH:14][C:9]=2[C:20]([CH3:25])([CH3:26])[O:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 866854881-(4-(2-(Ethoxymethoxy)propan-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone

Product 1

HCID 866854891-(1-Hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethanoneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-(2-(ethoxymethoxy)propan-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboro-lan-2-yl)phenyl)ethanone (684 mg, 1.89 mmol) in THF (15 mL) was added 6N HCl (10 mL). The reaction mixture was stirred at rt overnight. Water was added and the mixture was extracted with EA. The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (5:1) to give 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethanone (324 mg; yield 50% over 2 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.26 (b, 1H), 8.29 (s, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 2.61 (s, 3H), 1.44 (s, 6H) ppm; MS: m/z=205.1 (M+1, ESI+).

Workup

  1. extractionthe mixture was extracted with EA
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (5:1)

Sources & evidence

ORD record
ord-895b7b1cc402439a81c96ebe1aeaaea7
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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