Diethyl Ether → HCID 13419512, compound

HRID 1192458Notes

Reaction equation

HRID 1192458 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12](N(OC)C)=[O:13].[CH3:18][Mg]Br.CCOCC>O1CCCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12](=[O:13])[CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86656156HCID 86656156, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 13419512HCID 13419512, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-bromo-N-methoxy-N-methyl-2-naphthamide (0.708 g, 0.00241 mol) in tetrahydrofuran (10 mL) was added 3.00 M of methylmagnesium bromide in ether (8.19 mL, 0.0246 mol). The reaction was stirred at room temperature for 2 h, quenched with water at 0° C., then acidified with 1 N HCl, and extracted with EtOAc. The combined organic layers were washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated to dryness under reduced pressure. The residue was used directly in next step (488 mg, 81%). LCMS calculated for C12H10BrO(M+H)+: m/z=249.0.; found: 249.2.

Workup

  1. customquenched with water at 0° C.
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8ab1a41ef4fd4aec9580f0248253ca1d
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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