Sodium Thiosulfate → Ethyl 1-formylcyclopropanecarboxylate

HRID 494374

Reaction equation

HRID 494374 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+].CC1(C)N([O])C(C)(C)CCC1.[Br-].[Na+].Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH:9]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8][CH2:7]1)=[O:10]

Participants

8

Reactant 6

HCID 24477Sodium ThiosulfateHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylateHCID 23665760Sodium Hypochlorite

Product 1

HCID 9964122Ethyl 1-formylcyclopropanecarboxylateYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Preparation 232 1-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (3.00 g, 21.00 mmol) in dichloromethane (50 ml), at 0° C., was added saturated sodium hydrogen carbonate solution (50 ml), followed by TEMPO (659 mg, 4.00 mmol) and sodium bromide (400 mg, 4.00 mmol). After stirring for 5 min, sodium hypochlorite solution (10%, 14.00 mmol) was added slowly, followed by saturated sodium thiosulphate solution (50 ml). The two layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried (MgSO4) and concentrated in vacuo to give the titled compound (3.00 g).

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46dfd3ebaae1485283626fa6d6d3ca1d
Source dataset
uspto-grants-2009_05
Patent number
US07538134B2

Linked notes

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