Ethylene → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

HRID 890372노트

반응식

HRID 890372 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.O=S(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:20]=[CH2:21]>ClC(Cl)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH2:8][C:9](=[O:11])[CH2:21][CH2:20]2

참가 물질

7

반응물 4

HCID 6325EthyleneHCID 98372-(4-Fluorophenyl)acetic acidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 63651,1-Dichloroethane용매

반응 조건

온도
0 °C

실험 절차

4-fluorophenylacetic acid (1 equivalent) was dissolved in dichloroethane (1.3 M) containing SOCl2 (3 equivalents), the mixture was refluxed for 90 minutes and the solvent was removed. Solution of this crude product in CH2Cl2 was added dropwise within 60 minutes to AlCl3 (2 eq) in CH2Cl2 (0.4 M) while stirring at 0° C. Thereafter, ethylene was introduced at 0° C. over 45 minutes, whereupon the mixture was stirred further at room temperature for 1 hour, and thereafter was treated at 0° C. with ice-water. The organic phase was washed with 1 N HCl (2×), NaHCO3 (sat. sol.), dried and evaporated. The residue was triturated with hexane, yielding the product as a bright yellow solid.

후처리

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customthe solvent was removed
  3. stirringwas stirred further at room temperature for 1 hour
  4. washThe organic phase was washed with 1 N HCl (2×), NaHCO3 (sat. sol.)
  5. customdried
  6. customevaporated
  7. customThe residue was triturated with hexane

출처 및 근거

ORD 기록
ord-9b53831fa1fb4b54ae682bbb1bfc52a3
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995269B2

반응 노트

불러오는 중…