Diethyl Ether → HCID 76661290, compound

HRID 1616980Notes

Reaction equation

HRID 1616980 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.C(#N)C.C[Si]([CH:19]=[N+:20]=[N-:21])(C)C.C(OCC)C>C1COCC1>[N+:20](=[CH:19][C:9](=[O:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)=[N-:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 167693TrimethylsilyldiazomethaneHCID 13340573HCID 13340573, compound

Product 1

HCID 76661290HCID 76661290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 4-iodophenylacetyl chloride (12) obtained 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 (14 h) 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-iodophenyl)propan-2-one (13) as a pale yellow solid (635 mg, 4.44 mmol, 55.5%, 2 steps).

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-2c93d555379e4e41bac62bfd99787148
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

Loading…