Phenylacetyl chloride → Methyl 5-[4-(Phenylacetyl)phenyl]valerate

HRID 235194노트

반응식

HRID 235194 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:19]1([CH2:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=S)=S>[C:19]1([CH2:25][C:26]([C:4]2[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:2][CH:3]=2)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 7679Phenylacetyl chlorideHCID 262942Methyl 5-phenylpentanoateHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 23353739Methyl 5-[4-(Phenylacetyl)phenyl]valerate수율 66%

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

To a solution of 5.12 g of methyl 5-phenylvalerate in 25 ml of carbon disulfide, 7.10 g of anhydrous aluminium chloride was added under ice-cooling, and then 4.11 g of phenylacetyl chloride was added dropwise and stirring was continued at room temperature for 6 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride layer was washed successively with water, aqueous potassium carbonate solution and water, dried, and then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1) to afford 5.45 g of colorless crystals. Recrystallization from isopropyl ether gave colorless flakes, mp 53.5°~54° C.

후처리

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride layer was washed successively with water, aqueous potassium carbonate solution and water
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1)

출처 및 근거

ORD 기록
ord-cf89ed08037e4da49af3bb39c23e54ca
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597848

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