Sodium Thiosulfate → Methyl 4-formylcyclohexane-1-carboxylate

HRID 539314

반응식

HRID 539314 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.CCOCC>[CH:2]([CH:3]1[CH2:4][CH2:5][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)=[O:1]

참가 물질

7

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2회HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester2회

생성물 1

HCID 11252253Methyl 4-formylcyclohexane-1-carboxylate수율 99.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 4-(hydroxymethyl)cyclohexanecarboxylate (Intermediate 87, 4.08 g, 23.7 mmol) in DCM was added NaHCO3 (9.95 g, 118 mmol), followed by Dess-Martin Periodinane (12.1 g, 28.4 mmol). The mixture was stirred at r.t. for 2.5 h. Et2O (60 mL) was added followed by an aq. solution of NaHCO3 (1 M, 60 mL) and a 20% aq. solution of sodium thiosulfate (40 mL). The resulting mixture was stirred overnight. The phases were separated and the aqueous phase was extracted with Et2O. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (4.0 g, 99% yield): MS (EI) m/z 170 M+.

후처리

  1. stirringThe resulting mixture was stirred overnight
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with Et2O
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-86df18a157ec4625afd815265ab9d306
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865911B2

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