Diazomethane → HCID 54044568, compound

HRID 2293342Notes

Reaction equation

HRID 2293342 reaction equation
[CH2:1]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)(=O)[C:16]([Cl:18])=O.[N+:21](=[CH2:23])=[N-:22]>ClCCl.CN(C)C=O>[Cl:18][CH2:16][C:10]([C:9]1[CH:8]=[CH:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:14][CH:13]=1)=[O:12].[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:11])[CH:23]=[N+:21]=[N-:22])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 3

HCID 9550DiazomethaneHCID 334794-Pentylbenzoic acidHCID 65578Oxalyl chloride

Product 2

HCID 53822243HCID 53822243, compoundYield 1.3%HCID 54044568HCID 54044568, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 4-pentyl-benzoic acid (1.178 g, 6.13 mmol) and oxalyl chloride (630 uL, 855 mg, 6.74 mmol, 1.1 eq) in dichloromethane (15 mL) was stirred at 22° C. for 10 min, then treated with one drop of N,N-dimethylformamide at 22° C. {Caution, gas evolution may become brisk}. After gas evolution was no longer observed, the flask was fitted with a condenser and warmed to reflux for 30 min. The solution was cooled to -5° C., and cannulated into a cold (-5° C.), ethereal solution of diazomethane (40 mL). After the solution was stirred at -5° C. for 30 min, the flask was removed from the cold bath and the yellow solution was allowed to stir at 22° C. for 2 hrs (preferably in the dark). The solution was concentrated in vacuo, and purified by flash chromatography (5% ethyl acetate in hexane) to provide 33 mg (1.3%) of 2-chloro-4'-(n-pentyl) acetophenone and 586 mg (44%) of 4'-(n-pentyl) diazoacetophenone as a bright yellow oil.

Workup

  1. customthe flask was fitted with a condenser
  2. temperaturewarmed
  3. temperatureto reflux for 30 min
  4. customthe flask was removed from the cold bath
  5. stirringto stir at 22° C. for 2 hrs (preferably in the dark)
  6. concentrationThe solution was concentrated in vacuo
  7. custompurified by flash chromatography (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1925361e20a84bf0a7e4a77d1885fe93
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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