Hydrochloric Acid → HCID 66693368, compound

HRID 2367974Notes

Reaction equation

HRID 2367974 reaction equation
[OH-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16]([B:24]2[O:28][C:27]([CH3:30])(C)C(C)(C)[O:25]2)=[C:17]([C:20]([F:23])=[CH:21][CH:22]=1)C=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C[N+:34]([O-:36])=[O:35].Cl>O>[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16]2[B:24]([OH:25])[O:28][CH:27]([CH2:30][N+:34]([O-:36])=[O:35])[C:17]=2[C:20]([F:23])=[CH:21][CH:22]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 87421705HCID 87421705, compound

Product 1

HCID 66693368HCID 66693368, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaOH (48 mg, 1.20 mmol) was added to 3-(3-benzyloxy-propoxy)-6-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (500 mg, 1.2 mmol) in H2O (3 mL) at rt, and the reaction mixture was stirred at rt for 5 min. MeNO2 (219 mg, 3.6 mmol) was added dropwise and the mixture was stirred at rt for 16 h. The reaction mixture was acidified with 2 N HCl and extracted with EtOAc. The organic fraction was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. Purification was accomplished by flash chromatography (10-40% EtOAc/hexane) to give 120 mg of the title compound by 1H NMR spectrum. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.40-7.22 (m, 5H), 7.11 (t, J=8.8 Hz, 1H), 6.81 (t, J=8.6 Hz, 1H), 5.93 (dd, J=9.0, 2.3 Hz, 1H), 4.99 (dd, J=13.1, 2.5 Hz, 1H), 4.62-4.53 (m, 2H), 4.43 (dd, J=12.9, 9.0 Hz, 1H), 4.19-4.01 (m, 2H), 3.66 (dt, J=15.9, 5.7 Hz, 2H), 2.18-1.94 (m, 2H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −72.81 (s, 1F); MS (ESI) m/z=374 (M−1, negative).

Workup

  1. stirringthe mixture was stirred at rt for 16 h
  2. extractionextracted with EtOAc
  3. washThe organic fraction was washed with H2O
  4. dry with materialbrine, dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-98e9824b61044ce7b1eaacd192dd634e
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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