2-Chloro-N-methoxy-N-methylacetamide → HCID 86708713, compound

HRID 1751362Notes

Reaction equation

HRID 1751362 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])=[CH:7][CH:6]=[CH:5]2.C([Li])CCC.[Cl:28][CH2:29][C:30](N(OC)C)=[O:31]>O1CCCC1>[Cl:28][CH2:29][C:30]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][Si:13]([CH:14]([CH3:16])[CH3:15])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:3]=1)=[O:31]

Participants

5

Reactant 3

HCID 27347162-Chloro-N-methoxy-N-methylacetamideHCID 69672992HCID 69672992, compoundHCID 178418339Butyllithium

Product 1

HCID 86708713HCID 86708713, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (6-bromonaphthalen-1-yloxy)triisopropylsilane (10.4 g, 27.5 mmol) in tetrahydrofuran (180 mL) under argon at −78° C. was added n-butyllithium (2.5M in hexanes, 11.5 mL, 28.7 mmol). After stirring at this temperature for one hour, a solution of 2-chloro-N-methoxy-N-methyl acetamide (7.6 g, 55.2 mmol) in tetrahydrofuran (10 mL) was added to the reaction via cannula. The dry ice bath was removed and the reaction was allowed to warm to room temperature. After one hour at room temperature the reaction was diluted with ethyl acetate and the organics were washed with saturated aqueous NH4Cl solution, water and brine. The organic layer was dried (MgSO4) and concentrated, and the resulting residue was purified by flash chromatography to yield 2-chloro-1-(5-(triisopropylsilyloxy)-naphthalen-2-yl)ethanone (7.8 g, 75%) as a pale yellow oil.

Workup

  1. customThe dry ice bath was removed
  2. additionAfter one hour at room temperature the reaction was diluted with ethyl acetate
  3. washthe organics were washed with saturated aqueous NH4Cl solution, water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customthe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fda8618d507a450797e7cb097f8d1561
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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