Sodium Thiosulfate → Ethyl 1-formylcyclopropanecarboxylate

HRID 1848336Notes

Reaction equation

HRID 1848336 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:9][OH:10])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH:9]=[O:10])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Product 1

HCID 9964122Ethyl 1-formylcyclopropanecarboxylateYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere 1-Hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (5.0 g, 34.7 mmol) was dissolved in DCM (200 mL). NaHCO3 (11.7 g, 139 mmol) and Dess Martin periodinane (29.4 g, 69.4 mmol) were added. The suspension was stirred at rt for 30 min. A 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (200 mL) was added while keeping the temperature at 20° C. The mixture was stirred for 20 min followed by extraction with DCM (×2). The combined organic phases were dried (Na2SO4), filtered and concentrated to afford a crude product of 1-formyl-cyclopropanecarboxylic acid ethyl ester (5.1 g) which was used directly in the next step.

Workup

  1. customat 20° C
  2. stirringThe mixture was stirred for 20 min
  3. extractionfollowed by extraction with DCM (×2)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d4a275b153b46ca8ceffe026993f92e
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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