Hydrochloric Acid → HCID 19045524, compound

HRID 1591217Notes

Reaction equation

HRID 1591217 reaction equation
B.[O:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:7]([N:10]1[C:18]2[C:13](=CC(C=C)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])[CH3:8].O.O.C[N+]([O-])(C)C.Cl>C1COCC1.O>[C:7]([N:10]1[C:18]2[C:13](=[CH:3][C:4]([CH2:5][CH2:6][OH:2])=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 198430Trimethylamine oxide dihydrateHCID 2723981Borane;tetrahydrofuranHCID 19045508HCID 19045508, compound

Product 1

HCID 19045524HCID 19045524, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Borane-tetrahydrofuran complex (1.0M in THF, 20 ml, 20 mmol) was added dropwise to an ice cooled solution of 1-acetyl-2,3-dihydro-5-ethenyl-1H-indole (5.61 g, 30 mmol) in THF (150 ml). The mixture was stirred at 0° C. for 30 minute then at room temperature for 1 hr. Trimethylamine N-oxide dihydrate (8.88 g, 80 mmol) was added and the mixture was heated under reflux for 3 hr, cooled and poured into water (400 ml) and aqueous HCl (6N, 10 ml). The mixture was extracted with dichloromethane (3×400 ml) and the combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate, to give the alcohol as a white solid (3.41 g, 55%).

Workup

  1. waitat room temperature for 1 hr
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hr
  4. temperaturecooled
  5. extractionThe mixture was extracted with dichloromethane (3×400 ml)
  6. dry with materialthe combined organic fractions were dried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-def7e26afe4240e7b8fe3faf6231343a
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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