Oxalyl chloride → HCID 54421608, compound

HRID 1919415Notes

Reaction equation

HRID 1919415 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](O)=[O:4].C(Cl)(=O)C([Cl:19])=O>CN(C)C=O.ClCCl>[CH3:1][C:2]([CH3:15])([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([Cl:19])=[O:4]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 134782883-(Benzyloxy)-2,2-dimethylpropanoic acid

Product 1

HCID 54421608HCID 54421608, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Adapting procedures or variations thereof according to Lopez et al., Bioorg. & Med. Lett. 2003, 13(11), 1873-1878, a 500 mL round-bottomed flask equipped with a magnetic stirring bar was charged with 5.7 g (27.6 mmol) of 2,2-dimethyl-3-(phenylmethoxy)propanoic acid (26b), 20 mL of anhydrous dichloromethane (DCM), and 3 drops of N,N-dimethylformamide (DMF). Four-point-eight (4.8) mL (7.1 g, 55.2 mmol) of neat oxalyl chloride was slowly added to the solution. The reaction mixture was stirred at ca. 0° C. (ice-bath) for 5 hours. The solvents were removed under reduced pressure to provide the crude title compound (26c), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=1.34 (s, 6H), 3.54 (s, 2H), 4.56 (s, 2H), 7.29-7.37 (m, 5H) ppm. The analytical data was consistent with the proposed structure.

Workup

  1. custom2003, 13(11), 1873-1878, a 500 mL round-bottomed flask equipped with a magnetic stirring bar
  2. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-5f37501b4df74742a54bb8609bcfeea1
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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