Formic Acid → 5-Formylamino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran

HRID 234256Notes

Reaction equation

HRID 234256 reaction equation
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[C:12]=1[CH3:13].[CH:16](O)=[O:17]>>[CH:16]([NH:1][C:2]1[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]2[O:9][C:8]([CH3:10])([CH3:11])[CH2:7][C:6]=2[C:12]=1[CH3:13])=[O:17]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 100358625-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran

Product 1

HCID 107521185-Formylamino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuranYield 93.3%

Procedure

5-Amino-2,2,4,6,7- pentamethyl-2,3-dihydrobenzofuran (1.00 g, 4.87 mmol) was dissolved in formic acid (20 ml) and the solution was heated under reflux for 48 hours. The reaction mixture was concentrated under reduced pressure. Saturated sodium bicarbonate solution was added to the residue and the mixture was extracted with chloroform. The extract was washed with saturated saline, dried and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform-methanol, 97:3) to obtain the desired compound (1.06 g, yield: 93.3%). A part of it was recrystallized from dichloromethan-isopropyl ether to obtain white prisms, m.p. 177°-179° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 48 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionSaturated sodium bicarbonate solution was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe extract was washed with saturated saline
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (chloroform-methanol, 97:3)

Sources & evidence

ORD record
ord-78d87934f8e14db9b01957a520e94684
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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