Triethylamine → HCID 10730662, compound

HRID 234275Notes

Reaction equation

HRID 234275 reaction equation
C(N(CC)CC)C.Br[C:9]1[C:10]([CH3:23])=[C:11]([CH3:22])[C:12]2[O:16][C:15]([CH2:18][Br:19])([CH3:17])[CH2:14][C:13]=2[C:20]=1[CH3:21]>C(O)C.[C].[Pd]>[Br:19][CH2:18][C:15]1([CH3:17])[CH2:14][C:13]2[C:20]([CH3:21])=[CH:9][C:10]([CH3:23])=[C:11]([CH3:22])[C:12]=2[O:16]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 19078602HCID 19078602, compound

Product 1

HCID 10730662HCID 10730662, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Triethylamine (5.0 ml, 35.6 mmol) was added to a solution of 5-bromo-2-bromomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (12.4 g, 35.6 mmol) in ethanol (100 ml). Catalytic hydrogenation decomposition reaction was carried out on 5% palladium carbon under a hydrogen atmosphere. After the completion of the reaction, the catalyst was filtered and the filtrate was concentrated. The residue was dissolved in isopropyl ether, washed with water, dried and the solvent was distilled off. The residue was crystallized from methanol to obtain the desired compound (8.84 g, yield: 92.2%), m.p. 39°-40° C.

Workup

  1. customCatalytic hydrogenation decomposition reaction
  2. customAfter the completion of the reaction
  3. filtrationthe catalyst was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in isopropyl ether
  6. washwashed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-2eee10b31a814b8794957221e196d060
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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