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Methyl iodide → 2-Methoxymethylene-3,3-dimethyl-indan-1-one

HRID 495117
Notes
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Reaction equation

HRID 495117 reaction equation
[CH2:1]([O:3][CH:4]=O)[CH3:2].[H-].[Na+].C[C:9]1(C)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:18].[CH3:20]I>C1COCC1>[CH3:4][O:3][CH:1]=[C:2]1[C:17]([CH3:9])([CH3:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 3012022,2-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 686158752-Methoxymethylene-3,3-dimethyl-indan-1-one

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
3×

Procedure

Ethylformate (8.10 g, 110 mmol) in THF (50 ml) was added to the suspension of NaH (55% in mineral oil, 4.80 g, 110 mmol) in THF (50 ml). After stirring for 5 min at RT Dimethylindanone (16.0 g, 100 mmol)in THF (50 ml) was added. Gas evolution started and the temperature of the mixture rose and was controlled with an icebath to not exceed 40° C. After further stirring for 4.5 h at RT, methyl iodide (42.6 g, 300 mmol) was added und stirring continued for 48 h. After quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%) of was obtained.

Workup

  1. additionwas added
  2. customexceed 40° C
  3. stirringund stirring
  4. waitcontinued for 48 h
  5. customAfter quenching with aq. NaHCO3-solution and aqueous workup a dark red oil (20.4 g, 100%)
  6. customof was obtained

Sources & evidence

ORD record
ord-582895f1e2c74c1c9a827abc7c7859eb
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538243B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes