Diethyl Ether → 2-(1,1-Dimethylethoxy)-N-ethyl-1-naphthalenecarboxamide

HRID 1604233

Reaction equation

HRID 1604233 reaction equation
[Li]C(CC)C.C1CCCCC1.[CH2:12]([NH:14][C:15]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=[O:16])[CH3:13].CN(CCN(C)C)C.[Mg+2].[Br-].[Br-].CCOCC.C(OO[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])(=O)C1C=CC=CC=1>C1COCC1>[CH3:55][C:54]([CH3:57])([O:53][C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]=1[C:15]([NH:14][CH2:12][CH3:13])=[O:16])[CH3:56]

Participants

9

Reactant 7

HCID 3283Diethyl EtherHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 82241Magnesium BromideHCID 4088726N-ethyl-1-naphthalenecarboxamideHCID 21744378t-Butylperoxy benzoateHCID 178418400CID 53628100

Product 1

HCID 196023192-(1,1-Dimethylethoxy)-N-ethyl-1-naphthalenecarboxamideYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.3M s-BuLi in cyclohexane (34 mL, 44 mmol) was added dropwise to a -78° C. cooled solution of N-ethyl-1-naphthalenecarboxamide (20 mmol) and TMEDA (6.0 mL, 40 mmol) in THF (100 mL). After 30 min, MgBr2.Et2O (15.5 g, 60 mmol) was added portion wise, and the reaction was briefly warmed to ambient temperature then was recooled to -78° C. After 1 h at -78° C., t-butylperoxy benzoate (4.3 g, 22 mmol) was added. The resulting reaction was warmed to -30° C. and worked up in the usual manner, then was purified by chromatography with 3:7 ethyl acetate/hexanes to afford 1.7 g of desired compound as a white solid, a 33% yield. m.p. 126-127° C.

Workup

  1. customthen was recooled to -78° C
  2. waitAfter 1 h at -78° C.
  3. customThe resulting reaction
  4. temperaturewas warmed to -30° C.
  5. customwas purified by chromatography with 3:7 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9c54fa92272446849c5eb0d3d0b99cd6
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Linked notes

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