Cesium carbonate → 2-(3-(3-((1-Hydroxycyclooctyl)methoxy)phenyl)propyl)isoindoline-1,3-dione

HRID 875567노트

반응식

HRID 875567 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[O:22]1[C:24]2([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[OH:22][C:24]1([CH2:23][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])[CH:5]=[CH:6][CH:7]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 132407571-Oxaspiro[2.7]decaneHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

생성물 1

HCID 673176112-(3-(3-((1-Hydroxycyclooctyl)methoxy)phenyl)propyl)isoindoline-1,3-dione

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

A suspension of the phenol 58 (1.0 g, 3.5 mmol), 1-oxa-spiro[2.7]decane (0.5 g, 3.2 mmol) and Cs2CO3 (1.14 g, 3.5 mmol) in DMSO (4 mL) was heated at 120° C. for 16 h. After completion of reaction, the mixture was quenched by the addition of 1N HCl and extracted with DCM. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography (0 to 10% 7N NH3/methanol-CH2Cl2) afforded 2-(3-(3-((1-hydroxycyclooctyl)methoxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (1.057 g, 72%): 1H NMR (400 MHz, CDCl3) δ 7.10-7.36 (m, 2H), 6.40-6.80 (m, 6H), 3.69 (s, 2H), 2.10-2.45 (m, 2H), 1.30-2.0 (m, 18H).

후처리

  1. customAfter completion of reaction
  2. customthe mixture was quenched by the addition of 1N HCl
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0 to 10% 7N NH3/methanol-CH2Cl2)

출처 및 근거

ORD 기록
ord-05f7707efe134e9c982d374d13b0e435
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981153B2

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