3,4-dihydro-2H-pyran → 3-(5-chloro-1H-indol-3-yl)propan-1-ol

HRID 1777524Notes

Reaction equation

HRID 1777524 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>O.O1CCOCC1.C(OCC)(=O)C>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:16]=[C:15]2[CH2:14][CH2:13][CH2:12][OH:11]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Product 1

HCID 199793473-(5-chloro-1H-indol-3-yl)propan-1-olYield 64.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (4-chlorophenyl)hydrazine hydrochloride (5.26 g; 28.50 mmol) and 3,4-dihydro-2H-pyran (2.63 mL; 28.50 mmol) in a mixture of water (9 mL) and dioxane (36 mL) was stirred at 100° C. for 48 hours. After cooling to room temperature the mixture was diluted with ethyl acetate. The aqueous layer was separated and further extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane) to afford 3.85 g (64%) of 3-(5-chloro-1H-indol-3-yl)propan-1-ol as an oily residue.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-104743cb3b0d443c8550dd69d13e57f2
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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