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Methyl iodide → 1-[6-Benzyloxy-2-methoxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone

HRID 1766672
Notes
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Reaction equation

HRID 1766672 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([OH:18])[C:12]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](=O)([O-])[O-].[Cs+].[Cs+].CI>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([O:18][CH3:33])[C:12]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 211105611-[6-Benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone

Product 1

HCID 211105621-[6-Benzyloxy-2-methoxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanoneYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 1-[6-benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone (10.0 g) in tetrahydrofuran (15 mL) was added cesium carbonate (7.53 g) under ice-cooling, and then was added dropwise methyl iodide (2.88 mL). After stirring at room temperature overnight, the reaction mixture was evaporated under reduced pressure to dryness. Adding ethyl acetate (30 mL), the mixture was stirred for 30 min. The insoluble material was removed by filtration. The filtrate was evaporated under reduced pressure to dryness to give the title compound (10.2 g).

Workup

  1. temperaturecooling
  2. customthe reaction mixture was evaporated under reduced pressure to dryness
  3. stirringAdding ethyl acetate (30 mL), the mixture was stirred for 30 min
  4. customThe insoluble material was removed by filtration
  5. customThe filtrate was evaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-09103b6392d94bcd93a532444372f4f4
Source dataset
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07230031B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes