Formaldehyde → Ethyl 2,2-difluoro-3-hydroxypropanoate

HRID 1032914

反応式

HRID 1032914 の反応式
[CH2:1]=[O:2].[F:3][C:4]([F:11])(Br)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl-].[NH4+]>O1CCCC1.[Zn]>[F:3][C:4]([F:11])([CH2:1][OH:2])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 69585Ethyl bromodifluoroacetate

生成物 1

HCID 2758828Ethyl 2,2-difluoro-3-hydroxypropanoate

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of paraformaldehyde (4.5 g, 50 mmol), ethyl difluorobromoacetate (10.2 g, 50 mmol) and activated zinc dust (3.3 g, 40 mmol) in anhydrous tetrahydrofuran was heated under reflux for 0.5 h. Then the mixture was treated with a saturated aqueous solution of ammonium chloride and extracted with diethyl ether. After usual work-up the desired compound ethyl 2,2-difluoro-3-hydroxypropionate was obtained by flash chromatography on silica gel (ethyl acetate:hexane; 25:75) (4.1 g, 53%).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 h
  3. extractionextracted with diethyl ether

出典と根拠

ORDレコード
ord-ac3fae5763854e80b28e6ae53fb8b8f9
出典データセット
uspto-grants-1994_05
特許番号
US05308837

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