Acetyl chloride → HCID 22995208, compound

HRID 1167047Notes

Reaction equation

HRID 1167047 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(Cl)(=O)C.CCCC(CC(C1C=CC=CC=1)=O)CCCC.Cl.[NH2:37][OH:38].[CH2:39]([Li])[CH2:40][CH2:41][CH3:42].[CH2:44]([C:48]1[S:52][C:51](C(OC)=O)=[CH:50][CH:49]=1)[CH2:45][CH2:46]C>ClCCl.C(O)C.C(N(CC)CC)C.O1CCCC1>[CH2:39]([C:51]1[S:52][C:48]([C:44]2[O:38][N:37]=[C:46]([C:12]3[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=3)[CH:45]=2)=[CH:49][CH:50]=1)[CH2:40][CH2:41][CH3:42]

Participants

10

Reactant 6

HCID 6367Acetyl chlorideHCID 16607OctylbenzeneHCID 443297Hydroxyamine hydrochlorideHCID 14933666HCID 14933666, compoundHCID 53438266HCID 53438266, compoundHCID 178418339Butyllithium

Product 1

HCID 22995208HCID 22995208, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 22663003EtOH triethylamineSolvent

Procedure

Octylbenzene is acetylated with acetyl chloride in dichloromethane under AlCl3 catalysis and the resulting 4-octylacetophenone is converted into the corresponding oxime with hydroxylamine hydrochloride in ethanol/triethylamine. The oxime is dissolved in tetrahydrofuran under an inert gas atmosphere and doubly deprotonated with 2 equivalents of n-butyllithium. The solution is admixed with 0.5 equivalents of methyl 5-butyl-2-thiophenecarboxylate (obtained from 2-butylthiophene by lithiating with n-butyllithium in THF and reacting with carbon dioxide followed by esterification with methanol) and allowed to warm up to room temperature. Customary work-up followed by purification by recrystallization affords 5-(5-butylthiophen-2-yl)-3-(4-octylphenyl)-isoxazole; X 60 N 56 I.

Workup

  1. customCustomary work-up followed by purification by recrystallization

Sources & evidence

ORD record
ord-c74473119dbf4c2ba04642ca3892f755
Source dataset
uspto-grants-2003_09
Patent number
US06616989B1

Reaction notes

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