Dimethylacetamide → 5-(4-Chlorobenzyl)-2,2-dimethylcyclopentanone

HRID 1500147Notes

Reaction equation

COC([C:5]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]1=[O:12])=O.CN(C)C(=O)C.Cl.N1C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH:5]2[C:6](=[O:12])[C:7]([CH3:11])([CH3:10])[CH2:8][CH2:9]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 155 °C

Procedure

In 1-(4-chlorobenzyl)-3,3-dimethyl-2-oxocyclopentane carboxylic acid methyl ester (1.5 g, 0.00509 mol), N,N-dimethylacetamide (1.5 mL) and pyridine hydrochloride (0.706 g, 0.00509×1.2 mol) were added and stirred at 155° C. for 4 hours. In the reaction liquid, pyridine hydrochloride (0.177 g, 0.00509×0.3 mol) was added and further stirred at 155° C. for another 6 hours. In the reaction liquid, toluene and saturated sodium bicarbonate water were added, and the mixture was partitioned. After extracting the aqueous layer using toluene, the organic layer was dried using anhydrous sodium sulfate and concentrated. Thereafter, the dried and concentrated product was purified using a silica gel column, and a target product was obtained.

Workup

additionwas added
stirringfurther stirred at 155° C. for another 6 hours
additionwere added
customthe mixture was partitioned
extractionAfter extracting the aqueous layer
customthe organic layer was dried
concentrationconcentrated
customThereafter, the dried
customconcentrated product was purified
customa target product was obtained

Sources & evidence

ORD record: ord-f4a57ef729f04f1dba62e08ba995becf
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206106B2

Reaction notes

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