Acetone → HCID 22282695, compound

HRID 1374815Notes

Reaction equation

HRID 1374815 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[C:8]3[CH2:15][CH2:14][O:13][C:9]3=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=O)[CH3:2].B.CC(C)=O>O1CCCC1>[CH2:1]([C:4]1[C:12]2[C:7](=[C:8]3[CH2:15][CH2:14][O:13][C:9]3=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6331BoraneHCID 22282666HCID 22282666, compound

Product 1

HCID 22282695HCID 22282695, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 3-acetyl-7,8-dihydrofuro[2,3-g]indole (721 mg, 3.58 mmol) in tetrahydrofuran (25 mL) under an atmosphere of Ar at ambient temperature was added, over 5 min, borane (1.0 M in THF; 18 mL, 18 mmol). The resultant mixture was stirred at ambient temperature for 30 min, then heated to reflux for 2 h before cooling to room temperature. Acetone (25 mL) was added and the mixture was heated to reflux for a further 30 min. The mixture was cooled to room temperature then all solvent was removed in vacuo. Methanol (40 mL) was added, and the mixture was again heated to reflux for 30 min, then cooled to room temperature followed by solvent removal in vacuo. Purification by flash column chromatography [SiO2; ethyl acetate-heptane (1:4)] afforded the product (302 mg, 45%) as a white solid: m.p. 91–92.5° C.; Found: C, 76.90; H, 7.02; N, 7.44%. C12H13NO requires: C, 76.98; H, 7.00; N, 7.48%.

Workup

  1. additionwas added, over 5 min
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. temperaturethe mixture was heated
  5. temperatureto reflux for a further 30 min
  6. temperatureThe mixture was cooled to room temperature
  7. customall solvent was removed in vacuo
  8. additionMethanol (40 mL) was added
  9. temperaturethe mixture was again heated
  10. temperatureto reflux for 30 min
  11. temperaturecooled to room temperature
  12. customfollowed by solvent removal in vacuo
  13. customPurification by flash column chromatography [SiO2; ethyl acetate-heptane (1:4)]

Sources & evidence

ORD record
ord-4f19b76eb55f41ba8c38d4fe51d3c236
Source dataset
uspto-grants-2007_01
Patent number
US07166613B2

Reaction notes

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