Acetaldehyde → HCID 57625097, compound

HRID 888447Notes

Reaction equation

HRID 888447 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:16])[NH:12][CH2:13][CH2:14][N:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:17](=O)[CH3:18].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:17]([N:15]1[CH2:14][CH2:13][NH:12][C:11](=[O:16])[CH:10]1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:18]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 57625103HCID 57625103, compound

Product 1

HCID 57625097HCID 57625097, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

A 10-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with 31 (2.78 g, 12.7 mmol), acetaldehyde (727 mg, 16.5 mmol) and anhydrous methanol (40 mL). A solution of sodium cyanoborohydride (2.4 g, 38 mmol) and anhydrous zinc chloride (2.6 g, 19.1 mmol) in anhydrous methanol (40 mL) was added, and the reaction was stirred at room temperature for 1 h. After this time, 1N aqueous sodium hydroxide (25 mL) was added, and the methanol was evaporated under reduced pressure. The remaining aqueous solution was extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with water (100 mL) and brine (100 mL) and dried over magnesium sulfate. The drying agent was, removed by filtration and the filtrate concentrated under reduced pressure to afford a 98% yield (3.20 g) of 32 as a yellow oil: 1H NMR (500 MHz, DMSO-d6) δ 8.18 (d, 2H, J=8.5 Hz), 8.02 (d, 1H, J=4.0 Hz), 7.66 (d, 2H, J=8.5 Hz), 4.06 (s, 1H), 3.39 (td, 1H, J=12.0, 4.0 Hz), 3.22 (m, 1H), 3.07 (dt, 1H, J=12.0, 3.0 Hz), 2.50 (m, 1H), 2.37 (m, 1H), 2.21 (m, 1H), 0.91 (t, 3H, J=8.5 Hz); MS (ESI+) m/z 250 (M+H).

Workup

  1. customA 10-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customthe methanol was evaporated under reduced pressure
  4. extractionThe remaining aqueous solution was extracted with ethyl acetate (3×100 mL)
  5. washwashed with water (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. customremoved by filtration
  8. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f03495087f74defa8b14fd15bfb0af1
Source dataset
uspto-grants-2012_08
Patent number
US08247550B2

Reaction notes

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