Sodium hydride → (E)-3-[7-(1-phenylethoxy)-benzofuran-2-yl]-but-2-enoic acid-diethylamide

HRID 660420Notes

Reaction equation

HRID 660420 reaction equation
[H-].[Na+].[CH2:3]([N:5]([CH2:13][CH3:14])[C:6](=[O:12])[CH2:7]P(O)(O)=O)[CH3:4].[C:15]([C:18]1[O:22][C:21]2[C:23]([O:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])=[CH:24][CH:25]=[CH:26][C:20]=2[CH:19]=1)(=O)[CH3:16].[NH4+].[Cl-]>C1COCC1>[CH2:3]([N:5]([CH2:13][CH3:14])[C:6](=[O:12])/[CH:7]=[C:15](/[C:18]1[O:22][C:21]2[C:23]([O:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:29])=[CH:24][CH:25]=[CH:26][C:20]=2[CH:19]=1)\[CH3:16])[CH3:4]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 114032442-Acetyl-7-(1-phenylethoxy)benzo[b]furanHCID 18756985[(Diethylcarbamoyl)methyl]phosphonic acid

Product 1

HCID 11773324(E)-3-[7-(1-phenylethoxy)-benzofuran-2-yl]-but-2-enoic acid-diethylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

While replacing with nitrogen, NaH (0.13 g, 0.0054 mol) was suspended in absolute THF (20 mL), and N,N-diethylphosphonoacetamide (1.36 g, 0.0054 mol)/absolute THF (10 mL) was added dropwise at 0° C. Then, 2-acetyl-7-(1-phenylethoxy)benzo[b]furan (1.0 g, 0.0036 mol)/absolute THF (20 mL) was added dropwise. After stirring for 6 h while allowing to warm to room temperature, the disappearance of the starting materials was confirmed by TLC. The reaction mixture was poured into saturated aqueous NH4Cl solution, mixed and THF was evaporated under reduced pressure. The residue was extracted with ethyl acetate, washed with brine, dried over absolute magnesium sulfate, and evaporated under reduced pressure to give a pale-yellow oil. The obtained oil was purified by column chromatography to give the title compound as a pale-yellow oil. (0.75 g, 55.6%)

Workup

  1. additionmixed
  2. customTHF was evaporated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over absolute magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give a pale-yellow oil
  8. customThe obtained oil was purified by column chromatography

Sources & evidence

ORD record
ord-6a1d8ea801224706b1af478186b712b0
Source dataset
uspto-grants-2011_12
Patent number
US08084492B2

Reaction notes

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