Diethyl Ether → HCID 54230507, compound

HRID 1748900Notes

Reaction equation

HRID 1748900 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-c190c35cd9d1410cb0855247507e10a1
Source dataset
uspto-grants-2015_10
Patent number
US09151739B2

Reaction notes

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