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

HRID 1500147ノート

反応式

HRID 1500147 の反応式
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

参加物

6

反応物 4

HCID 31374DimethylacetamideHCID 10176127Pyridinium chloride2 回HCID 11449298HCID 11449298、化合物HCID 86585896Sodium bicarbonate water

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
155 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4a57ef729f04f1dba62e08ba995becf
出典データセット
uspto-grants-2015_12
特許番号
US09206106B2

反応ノート

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