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

HRID 19727Notes

Reaction equation

HRID 19727 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-ccfc1df5cea4484292ac30f4648842d3
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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