Sodium borohydride → 7-({4-[(4-hexylphenyl)ethynyl]anilino}methyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

HRID 551978Notes

Reaction equation

HRID 551978 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[C:9]([CH:12]=O)[CH:10]=[CH:11][C:5]=2[C:4](=[O:14])[O:3]1.[CH2:16]([C:22]1[CH:27]=[CH:26][C:25]([C:28]#[C:29][C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[BH4-].[Na+]>O>[CH2:16]([C:22]1[CH:27]=[CH:26][C:25]([C:28]#[C:29][C:30]2[CH:36]=[CH:35][C:33]([NH:34][CH2:12][C:9]3[CH:10]=[CH:11][C:5]4[C:4](=[O:14])[O:3][C:2]([CH3:15])([CH3:1])[O:7][C:6]=4[CH:8]=3)=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 57554470HCID 57554470, compoundHCID 575545514-[(4-Hexylphenyl)ethynyl]aniline

Product 1

HCID 575545407-({4-[(4-hexylphenyl)ethynyl]anilino}methyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-oneYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-7-carbaldehyde (700 mg; 3.38 mmol) and 4-[(4-hexylphenyl)ethynyl]aniline (940 mg; 3.38 mmol) in toluerene (40 mL) was refluxed for 48 hours with azeotropic removal of water. The solvent was removed under reduced pressure and the residue was taken up in a mixture of MeOH (20 mL) and THF (20 mL). NaBH4 (130 mg, 3.38 mmol) was added and the resulting mixture was stirred at rt for 8 hours. The solvents were removed under reduced pressure. The residue was taken up in EtOAc and washed with a saturated aqueous solution of NaACO3 and brine. The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give a brown oil. Purification by flash chromatography on silica (EtOAc:c-Hex 1:9 then 1:4) gave 466 mg (30%) of the title compound as a pale yellow oil. HPLC, Rt: 6.1 min (purity: 95.6%). LC/MS, M+(ESI: 468.0, M−(ESI): 466.1.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was taken up in a mixture of MeOH (20 mL) and THF (20 mL)
  3. customThe solvents were removed under reduced pressure
  4. washwashed with a saturated aqueous solution of NaACO3 and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent was removed under reduced pressure
  7. customto give a brown oil
  8. customPurification by flash chromatography on silica (EtOAc:c-Hex 1:9

Sources & evidence

ORD record
ord-a97944041e8d44a4a8f44830328d9a02
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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