Methyl Ethyl Ketone → 3-[4-(3-Di-n-butylaminopropoxy)benzoyl]-2-phenylbenzofuran

HRID 268343Notes

Reaction equation

HRID 268343 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:25]([N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32]Cl)[CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>CCOCC.O>[CH2:34]([N:29]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:30][CH2:31][CH2:32][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:7])=[CH:23][CH:24]=1)[CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 96084N-(3-Chloropropyl)dibutylamineHCID 13264991(4-Hydroxyphenyl)(2-phenyl-1-benzofuran-3-yl)methanone

Product 1

HCID 214353183-[4-(3-Di-n-butylaminopropoxy)benzoyl]-2-phenylbenzofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.0 g. (6.4 mmol.) of 3-(4-hydroxybenzoyl)-2-phenylbenzofuran, 1.3 g. (6.4 mmol.) of 3-di-n-butylaminopropyl chloride and 4.0 g. (0.04 mol.) of anhydrous potassium carbonate in 20 ml. of dry 2-butanone is refluxed for 18 hours. The reaction is cooled, water and ether are added and the layers are separated. The organic phase is extracted with 10% aqueous sodium hydroxide and the aqueous layers are combined and extracted again with water. The combined ether extracts are concentrated under reduced pressure to give the title compound.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureThe reaction is cooled
  3. customthe layers are separated
  4. extractionThe organic phase is extracted with 10% aqueous sodium hydroxide
  5. extractionextracted again with water
  6. concentrationThe combined ether extracts are concentrated under reduced pressure

Sources & evidence

ORD record
ord-53826219a097465b97c761cc54cc0b80
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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