Borane;tetrahydrofuran → Ethyl 3-(dimethylamino)-5-(hydroxymethyl)benzoate

HRID 2368873Notes

Reaction equation

HRID 2368873 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=1)[C:6](O)=[O:7].B.C1COCC1>C1COCC1>[CH3:17][N:2]([CH3:1])[C:3]1[CH:11]=[C:10]([CH:9]=[C:5]([CH2:6][OH:7])[CH:4]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 672577043-(Dimethylamino)-5-(ethoxycarbonyl)benzoic acid

Product 1

HCID 68335184Ethyl 3-(dimethylamino)-5-(hydroxymethyl)benzoateYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 1 (4 g, 16.86 mmol) in 40 mL of THF was added BH3.THF (1M in THF, 42.15 mL, 42.15 mmol) dropwise at 0° C. The mixture was refluxed for 4 hours and cooled to room temperature. The solvent was evaporated, diluted with EtOAc, and washed with saturated NaHCO3 and brine and dried with Na2SO4. The solution was filtered and concentrated. The residue was subjected to chromatography over silica gel (Hexanes/EtOAc=2/1) to give Compound 2 (2.95 g, 78%). 1H-NMR (500 MHz, CDCl3) δ 7.35 (s, 1H), 7.32 (s, 1H), 6.91 (s, 1H), 4.68 (s, 2H), 4.36 (q, J=7.1 Hz, 2H), 2.99 (s, 6H), 1.39 (t, J=7.1 Hz, 3H); 13C-NMR (125 MHz, CDCl3) δ 167.15, 150.71, 141.93, 131.36, 115.87, 114.91, 112.57, 65.41, 60.89, 40.54, 14.32; ESI-MS: m/z (MH+): 224.1281 (calc'd), 224.1283 (found).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customThe solvent was evaporated
  3. additiondiluted with EtOAc
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried with Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-591b05a456954e1e881be5dbb88722f7
Source dataset
uspto-grants-2014_04
Patent number
US08703815B2

Reaction notes

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