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

HRID 19727ノート

反応式

HRID 19727 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 28118Tetrafluoroboric acidHCID 167693Trimethylsilyldiazomethane2 回HCID 685612062-(2-Hydroxymethylindan-2-yl)-isoindole-1,3-dione

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-ccfc1df5cea4484292ac30f4648842d3
出典データセット
uspto-grants-2010_06
特許番号
US07745462B2

反応ノート

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