Methanol → Methyl 1-(2-iodophenyl)cyclobutanecarboxylate

HRID 592450Notes

Reaction equation

HRID 592450 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][CH2:9]1.OS(O)(=O)=O.[CH3:20]O>>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:12]([O:14][CH3:20])=[O:13])[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 867123261-(2-Iodophenyl)cyclobutanecarboxylic acid

Product 1

HCID 86712327Methyl 1-(2-iodophenyl)cyclobutanecarboxylate

Procedure

A solution of 1-(2-iodophenyl)cyclobutanecarboxylic acid A52 (425 mg, 1.41 mmol) in MeOH (25 mL) and conc. H2SO4 (1.0 mL) was stirred at 60° C. overnight. The volatiles were removed in vacuo and the resulting residue diluted in EtOAc (50 mL) and sat. soln. Na2CO3 (50 mL). The aqueous layer was extracted with EtOAc (3×50 mL), the combined organic fractions were dried (MgSO4) and the volatiles removed in vacuo to give the title compound A53 as a clear oil (361 mg, 81%). LCMS-A: rt 7.020 min; m/z 317 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe resulting residue diluted in EtOAc (50 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  4. dry with materialthe combined organic fractions were dried (MgSO4)
  5. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-418667bf85ae4ca591367710b0038fb8
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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