Diethyl Ether → HCID 76661292, compound

HRID 1616969Notes

Reaction equation

HRID 1616969 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=[O:11])=[CH:5][CH:4]=1.C[Si]([CH:19]=[N+:20]=[N-:21])(C)C.C(OCC)C>C1COCC1.C(#N)C>[N+:20](=[CH:19][C:10](=[O:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:14])([F:13])[F:1])=[CH:4][CH:5]=1)=[N-:21]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 148109432-(4-(Trifluoromethyl)phenyl)acetyl chloride

Product 1

HCID 76661292HCID 76661292, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, p-trifluoromethylphenylacetyl chloride (52) prepared above was dissolved in THF (2 mL) and acetonitrile (2 mL), and cooled to 0° C. To this was slowly added a solution of trimethylsilyldiazomethane in diethyl ether (2.0 M, 4.00 mL, 8.00 mmol), which was stirred overnight (20 hours) after warming up to room temperature. After being concentrated 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-(trifluoromethyl)phenyl]propan-2-one (53) as a pale yellow oily substance (666 mg, 2.92 mmol, 72.9%, 2 steps).

Workup

  1. concentrationAfter being concentrated 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-9826ad17da5d434e9fae52925cf6c39d
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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