6-Methoxy-2-naphthaldehyde → HCID 178440904, compound

HRID 1594945Notes

Reaction equation

HRID 1594945 reaction equation
[Mg:1].C(C1C=C([Br:12])C=CC=1)=C(C)C.CO[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=C[CH:19]=[C:20]([CH:25]=O)[CH:21]=2)[CH:16]=1>C1COCC1>[CH:21]([C:22]1[CH:17]=[C:16]([Mg:1][Br:12])[CH:15]=[CH:24][CH:23]=1)=[C:20]([CH3:25])[CH3:19]

Participants

5

Reactant 3

HCID 769916-Methoxy-2-naphthaldehydeHCID 5462224MagnesiumHCID 217068361-Bromo-3-(2-methyl-1-propenyl)benzene

Product 1

HCID 178440904HCID 178440904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of Rieke magnesium (0.12 g, 4.74 mmol; commercially available suspension) in dry THF (4.61 mL) was added neat 3-(iso-buten-1-yl)-phenylbromide (1.0 g, 4.74 mmol) at such a rate as to maintain a steady reflux. After the arylbromide was completely added, the reaction was refluxed under nitrogen for 0.5 hours. The solution was allowed to settle for 18 hours and the supernatant was determined to have a 0.56 m titer for active grignard by tritrating a known quantity of 2-methoxynaphthalene-6-carboxaldehyde.

Workup

  1. temperatureto maintain a steady reflux
  2. temperaturethe reaction was refluxed under nitrogen for 0.5 hours

Sources & evidence

ORD record
ord-465df1866a874a6884707d2ab3413212
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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