Hydrochloric Acid → HCID 66693560, compound

HRID 2368015Notes

Reaction equation

HRID 2368015 reaction equation
[OH-].[Na+].[N+:3]([CH3:6])([O-:5])=[O:4].[CH2:7]([O:9][C:10]1[C:11]([B:19]2[O:23][C:22](C)(C)C(C)(C)[O:20]2)=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])C=O)[CH3:8].Cl>O.C1COCC1>[CH2:7]([O:9][C:10]1[C:11]2[B:19]([OH:20])[O:23][CH:22]([CH2:6][N+:3]([O-:5])=[O:4])[C:12]=2[CH:15]=[CH:16][C:17]=1[F:18])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 86664749HCID 86664749, compound

Product 1

HCID 66693560HCID 66693560, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of sodium hydroxide (80 mg, 2.0 mmol) in water (3.0 mL), nitromethane (244.0 mg, 4.0 mmol) was added at 0° C. and stirred for 10 min. Then 3-ethoxy-4-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (588.0 mg, 2.0 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at for 1 h at 0° C. and for 2 h at room temperature. The reaction mixture was acidified with 2.5 M HCl (1.0 mL) and the product was extracted with ethyl acetate (2×20 mL). The organic extracts were combined and washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and product was chromatographed on a column of silica gel(CH2Cl2:MeOH=95:5) to give the title compound as a solid (350 mg, 69%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 7.40 (dd, J=11.3, 8.2 Hz, 1H), 7.16 (dd, J=8.0, 3.3 Hz, 1H), 5.74 (d, J=9.0 Hz, 1H), 5.30 (dd, J=13.5, 2.2 Hz, 1H), 4.62 (dd, J=13.5, 9.2 Hz, 1H), 4.35 (q, J=6.8 Hz, 2H), 1.28 (t, J=6.8 Hz, 3H); MS (ESI) m/z=254 (M−1, negative).

Workup

  1. stirringThe reaction mixture was stirred at for 1 h at 0° C. and for 2 h at room temperature
  2. extractionthe product was extracted with ethyl acetate (2×20 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure and product
  6. customwas chromatographed on a column of silica gel(CH2Cl2:MeOH=95:5)

Sources & evidence

ORD record
ord-264cafb819f14fa08ac3f3b5140f00c9
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

Loading…