Ammonium Chloride → 5-Benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran

HRID 2186261Notes

Reaction equation

HRID 2186261 reaction equation
C([Li])CCC.[Br-].[CH2:7]([PH2+]C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:21]([O:28][C:29]1[CH:30]=[CH:31][C:32]2[O:36][C:35]([CH:37]=O)=[CH:34][C:33]=2[C:39]=1[C:40]([CH3:43])([CH3:42])[CH3:41])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:21]([O:28][C:29]1[CH:30]=[CH:31][C:32]2[O:36][C:35]([CH:37]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:34][C:33]=2[C:39]=1[C:40]([CH3:41])([CH3:43])[CH3:42])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 23442876n-Heptylphenylphosphonium bromideHCID 234428795-Benzyloxy-4-t-butyl-2-formylbenzofuranHCID 178418339Butyllithium

Product 1

HCID 543087225-Benzyloxy-4-t-butyl-2-(1-octenyl)benzofuranYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen atmosphere, 2.6 ml of n-butyl lithium (1.6 M in n-pentane) was added dropwise to a suspension of 1.84 g of n-heptylphenylphosphonium bromide in 10 ml of tetrahydrofuran. After stirring at room temperature for 30 minutes, a solution of 1.0 g of 5-benzyloxy-4-t-butyl-2-formylbenzofuran synthesized in Example 2-2) in 10 ml of tetrahydrofuran was added dropwise. Then, the mixture was heated under reflux for 30 minutes, cooled and then combined with a saturated aqueous ammonium chloride solution and extracted with chloroform. The organic layers were dried over anhydrous magnesium sulfate, then concentrated, and the residue was purified by silica gel column chromatography (in chloroform) to give 1.14 g of 5-benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran as a colorless oil (yield 91%). 1H NMR (60 MHz, CDCl3) δ ppm: 0.89 (t, 3H, J=6.0 Hz), 1.13-1.72 (m, 8H), 1.56 (s, 9H), 1.93-2.62 (m, 2H), 5.03 (s, 2H), 6.02-6.40 (m, 2H), 6.78-7.46 (m, 8H).

Workup

  1. temperatureThen, the mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturecooled
  4. extractionextracted with chloroform
  5. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel column chromatography (in chloroform)

Sources & evidence

ORD record
ord-3bb8ee7a2a794e9394765fef04fceec9
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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