Triacetoxyperiodinane → Methyl 6-formylpyridine-3-carboxylate

HRID 341519

反応式

HRID 341519 の反応式
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]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 7894146-Hydroxymethyl-nicotinic acid methyl ester2 回

生成物 1

HCID 586269Methyl 6-formylpyridine-3-carboxylate収率 105%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b231342f377b4faeb25c62d2e8ca62f1
出典データセット
uspto-grants-2014_11
特許番号
US08895733B2

関連ノート

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