Methanol → HCID 59395065, compound

HRID 383361Notes

Reaction equation

HRID 383361 reaction equation
[CH:1]1([C:6]2[C:7]([OH:19])=[CH:8][C:9]([N+:16]([O-:18])=[O:17])=[C:10]([CH2:12][C:13]([OH:15])=[O:14])[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH3:24]O>ClCCl>[CH:1]1([C:6]2[C:7]([OH:19])=[CH:8][C:9]([N+:16]([O-:18])=[O:17])=[C:10]([CH2:12][C:13]([O:15][CH3:24])=[O:14])[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 59395048HCID 59395048, compound

Product 1

HCID 59395065HCID 59395065, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-cyclopentyl-4-hydroxy-2-nitro-phenyl)acetic acid (270 mg, 1.02 mmol) in methanol was added thionyl chloride (149 μL, 2.04 mmol) dropwise at 25° C. The mixture was stirred at room temperature for 1 h. The reaction was diluted with dichloromethane and washed with 50% saturated NaHCO3 (2×50 mL), brine, dried over Na2SO4, and concentrated in vacuo to afford methyl 2-(5-cyclopentyl-4-hydroxy-2-nitro-phenyl)acetate as clear brown oil (180 g, 63% yield). LC/MS m/z 280.0 [M+H]+.

Workup

  1. washwashed with 50% saturated NaHCO3 (2×50 mL), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49701417ccf1473fa238c6f9267a53a6
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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