Water → 2-(2-Methoxymethylindan-2-yl)-isoindole-1,3-dione

HRID 19727노트

반응식

HRID 19727 반응식
[CH3:1][Si](C=[N+]=[N-])(C)C.[OH:8][CH2:9][C:10]1([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1.F[B-](F)(F)F.[H+].O>C(Cl)Cl>[CH3:1][O:8][CH2:9][C:10]1([N:19]2[C:20](=[O:29])[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]2=[O:28])[CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:18]1

참가 물질

6

반응물 4

HCID 962WaterHCID 28118Tetrafluoroboric acidHCID 167693Trimethylsilyldiazomethane2회HCID 685612062-(2-Hydroxymethylindan-2-yl)-isoindole-1,3-dione

생성물 1

HCID 685632312-(2-Methoxymethylindan-2-yl)-isoindole-1,3-dione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(Trimethylsilyl)diazomethane (2 M hexanes, 0.51 ml, 1.03 mmol) is added dropwise to a cooled (0° C.) solution of 2-(2-hydroxymethylindan-2-yl)-isoindole-1,3-dione (0.150 g, 0.511 mmol) and fluoroboric acid (48% aqueous, 93.5 μl, 0.511 mmol) in CH2Cl2 (4 ml). The reaction is stirred for 20 minutes, then three further portions of (trimethylsilyl)diazomethane (2 M hexanes, 0.128 ml, 0.25 mmol; 64 μl, 0.12 mol; 64 μl, 0.12 mmol)) are made at 20 minute intervals. The reaction is stirred for a further 40 minutes after the final addition, poured into water and extracted with dichloromethane. The organic phase is washed with brine, dried (MgSO4) and evaporated. The crude product is purified by flash chromatography (CH2Cl2 elution) to afford 2-(2-methoxymethylindan-2-yl)-isoindole-1,3-dione, MH+308.

후처리

  1. stirringThe reaction is stirred for a further 40 minutes after the final
  2. additionaddition
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product is purified by flash chromatography (CH2Cl2 elution)

출처 및 근거

ORD 기록
ord-ccfc1df5cea4484292ac30f4648842d3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745462B2

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