Sodium Thiosulfate → Ethyl 1-formylcyclopropanecarboxylate

HRID 494374

반응식

HRID 494374 반응식
[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]

참가 물질

8

반응물 6

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

생성물 1

HCID 9964122Ethyl 1-formylcyclopropanecarboxylate수율 100.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-46dfd3ebaae1485283626fa6d6d3ca1d
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538134B2

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