Diethyl Ether → HCID 54230507, compound

HRID 1616971Notes

Reaction equation

HRID 1616971 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=[O:11])=[CH:5][CH:4]=1.C(#N)C.C[Si]([CH:20]=[N+:21]=[N-:22])(C)C.C(OCC)C>C1COCC1>[N+:21](=[CH:20][C:10](=[O:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[N-:22]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 167693TrimethylsilyldiazomethaneHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 54230507HCID 54230507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 4-methoxyphenylacetyl chloride (61) (952 mg, 5.16 mmol) was dissolved in THF (2.5 mL) and acetonitrile (2.5 mL) and cooled to 0° C. To this was slowly added a solution of trimethylsilyldiazomethane in diethyl ether (2.0 M, 5.00 mL, 10.0 mmol), which was stirred overnight (15 hours) after warming up to room temperature. After concentrating under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/diethyl ether═1/1) to give 1-diazo-3-(4-methoxyphenyl)propan-2-one (62) as a pale yellow oily substance (692 mg, 3.64 mmol, 70.6%).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue was purified by silica gel flash column chromatography (n-hexane/diethyl ether═1/1)

Sources & evidence

ORD record
ord-08218f8012744593a452a4a1390fd67b
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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