Hydrochloric Acid → HCID 57969084, compound

HRID 1471616Notes

Reaction equation

HRID 1471616 reaction equation
O1CCCCC1OC[C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[B:24]1[O:28]C(C)(C)[C:26](C)(C)[O:25]1)[O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.Cl.C([O-])(O)=O.[Na+]>CCO>[OH:28][B:24]1[C:23]2[CH:9]=[CH:10][C:11]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH:17]=[O:18])=[CH:19][CH:20]=3)=[CH:21][C:22]=2[CH2:26][O:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57968741HCID 57968741, compound

Product 1

HCID 57969084HCID 57969084, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-[3-(tetrahydro-pyran-2-yloxymethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-benzaldehyde (1.4 g, 3.2 mmol, 1.0 eq.) in EtOH (15 mL) at 0° C. was added HCl (15 mL, 3N). The mixture was stirred at 0° C. for 20 minutes and allowed to warm to room temperature in another 1 h. The mixture was then treated with sat. NaHCO3 drop wise until PH reaching 7. The precipitate was collected by filtration, washed with H2O to give 4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-benzaldehyde as a white solid. LCMS (m/z) 255 (M+H); 1H NMR (DMSO-d6) δ: 9.92 (s, 1H), 9.19 (s, 1H), 7.92 (d, J=8.8 Hz, 1H), 7.92 (q, J=4.6 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.16 (d, J=8.7 Hz, 2H), 7.12-7.19 (m, 1H), 7.09 (dd, J=8.0, 2.1 Hz, 1H), 4.95 (s, 2H).

Workup

  1. temperatureto warm to room temperature in another 1 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with H2O

Sources & evidence

ORD record
ord-3e3e2e6b15a1483dbb67782962f7acaf
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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