Diethyl Ether → 1-Diazonio-3-(3-methoxyphenyl)prop-1-en-2-olate

HRID 1616974Notes

Reaction equation

HRID 1616974 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:7][CH:8]=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:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[N-:22]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 167693TrimethylsilyldiazomethaneHCID 27332463-Methoxyphenylacetyl chloride

Product 1

HCID 713384101-Diazonio-3-(3-methoxyphenyl)prop-1-en-2-olate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 3-methoxyphenylacetyl chloride (81) (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═3/2) to give 1-diazo-3-(3-methoxyphenyl)propan-2-one (82) as a pale yellow oily substance (650 mg, 3.42 mmol, 66.3%).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue was purified by silica gel flash column chromatography (n-hexane/diethyl ether═3/2)

Sources & evidence

ORD record
ord-7002e553efc94aa1a90ab89f4113ddbf
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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