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

HRID 1500147노트

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HRID 1500147 반응식
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

참가 물질

6

반응물 4

HCID 31374DimethylacetamideHCID 10176127Pyridinium chloride2회HCID 11449298HCID 11449298, 화합물HCID 86585896Sodium bicarbonate water

생성물 1

HCID 114248965-(4-Chlorobenzyl)-2,2-dimethylcyclopentanone

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
155 °C

실험 절차

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.

후처리

  1. additionwas added
  2. stirringfurther stirred at 155° C. for another 6 hours
  3. additionwere added
  4. customthe mixture was partitioned
  5. extractionAfter extracting the aqueous layer
  6. customthe organic layer was dried
  7. concentrationconcentrated
  8. customThereafter, the dried
  9. customconcentrated product was purified
  10. customa target product was obtained

출처 및 근거

ORD 기록
ord-f4a57ef729f04f1dba62e08ba995becf
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206106B2

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