Sodium Thiosulfate → Ethyl 1-formylcyclopropanecarboxylate

HRID 238164

反応式

HRID 238164 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[OH:23][CH2:24][C:25]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(=O)(O)[O-].[Na+]>[CH:24]([C:25]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][CH2:26]1)=[O:23]

参加物

6

反応物 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

生成物 1

HCID 9964122Ethyl 1-formylcyclopropanecarboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

At 0° C., 5.05 g (11.9 mmol) of Dess-Martin periodane reagent were added to a solution of 1.225 g (8.5 mmol) of ethyl 1-hydroxymethylcyclopropanecarboxylate [for the preparation see, for example, T. A. Ayers, Tetrahedron Lett. 40 (30), 5467-5470 (1999)] in 43 ml of dichloromethane, and the mixture was then stirred at RT for 6 h. A solution of 6.7 g (42.5 mmol) of sodium thiosulfate in 60 ml of saturated aqueous sodium bicarbonate solution was then added to the reaction mixture. The mixture was stirred at RT for 20 min, and the phases were then separated. The organic phase was washed twice with water, dried over magnesium sulfate and concentrated at 20° C. under reduced pressure. This gave 1.139 g (80.0% of theory) of the target compound.

後処理

  1. customthe phases were then separated
  2. washThe organic phase was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated at 20° C. under reduced pressure

出典と根拠

ORDレコード
ord-372b0b3a5298469fabb56dbe3c5bb069
出典データセット
uspto-grants-2014_02
特許番号
US08642592B2

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