Hydrochloric Acid → HCID 58292699, compound

HRID 1798068Notes

Reaction equation

HRID 1798068 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:18]C3CCCCO3)[CH:14]=[C:15]([O:16][CH3:17])[C:7]1=2)[CH3:2].Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([O:16][CH3:17])[C:7]1=2)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67252189HCID 67252189, compound

Product 1

HCID 58292699HCID 58292699, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl-2-(1-hydroxy-4-methoxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.35 g, 1.0 mmol) in THF (10 mL) was added dropwise concentrated hydrochloride acid (0.2 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hr and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/PE=1/2) to give the title compound as a light yellow solid (180 mg, Y: 67.7%). 1H NMR (400 MHz, DMSO-d) δ 9.45 (s, 1H), 9.15 (s, 1H), 6.65-6.66 (d, J=1.2 Hz, 1H), 6.48-6.49 (d, J=1.2 Hz, 1H), 5.33-5.36 (m, 1H), 4.05-4.10 (m, 2H), 3.76 (s, 3H), 3.10-3.13 (m, 1H), 2.15-2.21 (m, 1H), 1.16-1.20 (m, 3H). MS (ESI) m/z=267 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (EtOAc/PE=1/2)

Sources & evidence

ORD record
ord-3cbcf78f4e7241129d4b97da4c86d287
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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