Triacetoxyperiodinane → Methyl 6-formylpyridine-3-carboxylate

HRID 341519

반응식

HRID 341519 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[CH:24]([C:25]1[N:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1)=[O:23]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 7894146-Hydroxymethyl-nicotinic acid methyl ester2회

생성물 1

HCID 586269Methyl 6-formylpyridine-3-carboxylate수율 105%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Dess-Martin periodinane (2.54 g, 5.98 mmol) was added to a solution of methyl 6-(hydroxymethyl)pyridine-3-carboxylate (Intermediate 190, 1.00 g, 5.98 mmol) in DCM (75 mL) at room temperature. The reaction mixture was stirred at room temperature for 24 hrs before being diluted with DCM (50 mL), washed with a 1:1 mixture of saturated aqueous solution of sodium bicarbonate and sodium thiosulfate (3×75 mL). The organic phase was dried over sodium sulfate, filtered and evaporated under vacuum to provide the title compound (1.02 g, 105%). Method B HPLC-MS: MH+ requires m/z=166 Found: m/z=166, Rt=1.44 min (62%).

후처리

  1. washwashed with a 1:1 mixture of saturated aqueous solution of sodium bicarbonate and sodium thiosulfate (3×75 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-b231342f377b4faeb25c62d2e8ca62f1
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895733B2

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