3-Chlorobenzaldehyde → cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide

HRID 510623

반응식

HRID 510623 반응식
[Br-].[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]1[CH2:13][CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=O.CC(C)([O-])C.[K+]>O1CCCC1>[Cl:35][C:36]1[CH:37]=[C:38](/[CH:39]=[CH:15]\[CH2:14][CH2:13][N:4]2[C:5](=[O:12])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]2=[O:2])[CH:41]=[CH:42][CH:43]=1

참가 물질

5

반응물 3

HCID 114773-ChlorobenzaldehydeHCID 22018487(3-(1,3-Dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 58679826cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-75 °C

실험 절차

To a stirred suspension of (3-(1,3-dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromide (17.6 g, 33.2 mmol) in tetrahydrofuran (170 mL) at ambient temperature was added 3-chlorobenzaldehyde (3.76 mL, 33.2 mmol), and the resulting mixture was cooled with a dry-ice acetone bath to −75° C. Solid potassium t-butoxide (3.72 g, 33.2 mmol) was added, and stirring was continued in the bath for an additional 20 minutes; the temperature was −80° C. The cooling bath was removed, and when the internal temperature reached −30° C., the flask was placed in a water-ice bath. The temperature eventually settled at 10° C. and was maintained for 2 hours. The reaction mixture was poured into a separatory funnel containing water (250 mL), and this was extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 90/10 hexanes/ethyl acetate, to afford (Z)-2-(4-(3-chlorophenyl)but-3-enyl)isoindoline-1,3-dione as a white solid (8.46 g, 82% yield).

후처리

  1. customwas −80° C
  2. customThe cooling bath was removed
  3. customreached −30° C.
  4. customthe flask was placed in a water-ice bath
  5. customeventually settled at 10° C.
  6. temperaturewas maintained for 2 hours
  7. additionThe reaction mixture was poured into a separatory funnel
  8. additioncontaining water (250 mL)
  9. extractionthis was extracted with ethyl acetate (250 mL)
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by chromatography on silica gel
  13. washeluting with 90/10 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-d88aa51af29e45db999f2ad28496616a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096567B2

연결된 노트

불러오는 중…