Acetic Acid → HCID 68520215, compound

HRID 452293Notes

Reaction equation

HRID 452293 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=[O:7].[N+:12]([CH2:15][CH3:16])([O-:14])=[O:13].[OH-].[Na+].C(O)(=O)C>CO>[F:11][C:10]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH:15]([N+:12]([O-:14])=[O:13])[CH3:16])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 14798Sodium HydroxideHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 68520215HCID 68520215, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a flame dried 100 mL round bottom flask was added 3-methoxy-4-fluorobenzaldehyde (367 mg, 2.38 mmol) and this was dissolved in methanol (23 mL). The reaction solution was cooled to 0° C. and nitroethane (357 mg, 4.76 mmol) was added to it followed by 5M NaOH (0.476 mL, 2.38 mmol). The solution was stirred for 80 min at 0° C. after which acetic acid (2% solution, 32 mL) was added and stirred for an additional 30 min. The reaction mixture was concentrated and water (10 mL) was added. The solution was extracted with dichloromethane (4×20 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, and concentration to give afford an oil which was purified by silica gel flash chromatography using dichloromethane as eluant. Product (391 mg, 72%) product Was obtained as a colorless oil in a 1.88:1 ratio (A:B) of diastereomers. Pair A: 1H NMR (600 MHz, CDCl3): δ 7.07 (m, 1H), 7.0 (m, 1H), 6.8 (m, 1H), 5.34 (t, 1H, J=3 Hz), 4.65 (d of q, 1H, J=3.6, 6.6 Hz), 3.9 (s, 3H), 2.697 (d, 1H, J=3.6 Hz), 1.5 (d, 3H, J=6.6 Hz). 13C NMR (75 MHz, CDCl3): δ 153.3, 150.1, 147.44 (d, J=10.8 Hz), 134.1, 117.7 (d, J=7 Hz), 115.7 (d, J=18.6 Hz), 110.6, 86.8, 72.8, 55.8, 11.7. Pair B: NMR (600 MHz, CDCl3): δ 7.07 (m, 1H), 7.0 (m, 1H), 6.8 (m, 1H), 4.9 (d Of d, 1H, J=3.6, 9 Hz), 4.72 (m, 1H), 3.9 (s, 3H), 2.57 (d, 1H, J=4.2 Hz), 1.33 (d, 3H, J=5.4 Hz). 13C NMR (75 MHz, CDCl3): δ 153.8, 150.5, 147.76 (d, J=10.8 Hz), 134.1, 119 (d, J=7 Hz), 115.8 (d, J=18.6 Hz), 111, 87.7, 75.3, 55.8, 15.9. HRMS: Calc'd for C10H12FNO4 (M+Na): 252.0642; Found: 252.0643.

Workup

  1. customTo a flame dried 100 mL round bottom flask
  2. additionwas added
  3. concentrationThe reaction mixture was concentrated
  4. additionwater (10 mL) was added
  5. extractionThe solution was extracted with dichloromethane (4×20 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate, and concentration
  8. customto give
  9. customafford an oil which
  10. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-68e4277f06fa4c6eb333da9eb6aaaa8b
Source dataset
uspto-grants-2013_07
Patent number
US08491868B2

Reaction notes

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