4-tert-Butylbenzaldehyde → HCID 11585104, compound

HRID 551908Notes

Reaction equation

HRID 551908 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]([C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:34]([C:38]1[CH:39]=[CH:40][C:41]([CH2:42][N:18]([CH2:17][C:16]2[CH:32]=[CH:33][C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=3)=[CH:14][CH:15]=2)[C:19]2[CH:31]=[CH:30][C:22]3[O:23][C:24]([CH3:29])([CH3:28])[O:25][C:26](=[O:27])[C:21]=3[CH:20]=2)=[CH:44][CH:45]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 703244-tert-ButylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 114761686-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 11585104HCID 11585104, compoundYield 35.6%

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 4-tert-butylbenzaldehyde (Aldrich, 85 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 71 mg (31%) of the title compound as a yellow oil. HPLC, Rt: 6.4 min (purity: 86.3%). 1H NMR (CDCl3) δ: 7.85-6.90 (m, 15H), 4.62 (brs, 4H), 2.62 (t, J=7.6 Hz, 2H), 1.70 (s, 6H), 1.61 (m, 2H), 1.33 (m, 2H), 1.30 (s, 9H), 0.93 (t, J=7.2 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-b073b74e4e774ea4aaa107e36d17009d
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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