1-Naphthaldehyde → HCID 11585057, compound

HRID 551902Notes

Reaction equation

HRID 551902 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][C:19]3[CH:31]=[CH:30][C:22]4[O:23][C:24]([CH3:29])([CH3:28])[O:25][C:26](=[O:27])[C:21]=4[CH:20]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:34]1([CH:44]=O)[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][N:18]([CH2:44][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=3)[C:19]3[CH:31]=[CH:30][C:22]4[O:23][C:24]([CH3:29])([CH3:28])[O:25][C:26](=[O:27])[C:21]=4[CH:20]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 114761686-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 11585057HCID 11585057, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 6-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one (150 mg, 0.34 mmol) in anhydrous DCE (3 mL) were added 1-naphtaldehyde (Fluka, 70 μL, 0.51 mmol) and sodium triacetoxyborohydride (110 mg, 0.51 mmol). The reaction mixture was stirred at rt for 72 hrs. The solvent was removed under reduced pressure. The residue was taken up with an aqueous solution of NaOH (2 mL, 1N) and extracted with Et2O (6 ml). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Purification by flash chromatography on silicagel (pentane/DCM (2/3)) gave 72 mg (36%) of the title compound as a yellow oil. HPLC, Rt: 6.2 min (purity: 100%). 1H NMR (CDCl3) δ: 7.91-7.80 (m, 3H), 7.54-7.27 (m, 11H), 7.17 (d, J=7.9 Hz, 2H), 7.08 (m, 1H), 6.78 (d, J=8.7 Hz, 1H), 5.20 (s, 2H), 4.70 (s, 2H), 2.63 (t, J=7.7 Hz, 2H), 1.69 (s, 6H), 1.61 (m, 2H), 1.37 (m, 2H), 0.94 (t, J=7.4 Hz, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with Et2O (6 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customPurification by flash chromatography on silicagel (pentane/DCM (2/3))

Sources & evidence

ORD record
ord-82829a674ffb4670a129fe7125ff3cf8
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

Loading…