Butyryl chloride → HCID 21914106, compound

HRID 887933Notes

Reaction equation

HRID 887933 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13](=[NH:16])[NH:14][OH:15])(=[O:3])[CH3:2].[C:17](Cl)(=O)[CH2:18][CH2:19][CH3:20]>N1C=CC=CC=1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]1[N:16]=[C:17]([CH2:18][CH2:19][CH3:20])[O:15][N:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 178473715HCID 178473715, compound

Product 1

HCID 21914106HCID 21914106, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of intermediate (14) (0.00898 mole) and butanoyl chloride (0.0094 mole) in pyridine (140 ml) was stirred at room temperature for 40 hours and then heated to reflux. After 21 hours the reaction was cooled and concentrated in vacuo. The residue was extracted between DCM and saturated aqueous NaHCO3 and the organic fraction was dried over Na2SO4, filtered, and concentrated. The residue was subjected to silica gel flash column chromatography (eluent 100% CH2Cl2 to 95/5 CH2Cl2/ether), yielding 1-acetyl-2,3-dihydro-2-(5-propyl-1,2,4-oxadiazol-3-yl)-1H-indole (compound 89, mp. 93-94° C.).

Workup

  1. temperatureheated to reflux
  2. temperatureAfter 21 hours the reaction was cooled
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted between DCM and saturated aqueous NaHCO3
  5. dry with materialthe organic fraction was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de2b6d1b8f7e4f14b728091b86111b6e
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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