Water → 2-(1-cyclopropylethoxy)Acetic acid

HRID 376353

反応式

HRID 376353 の反応式
[H-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].[CH3:8][CH:9]([CH:11]1[CH2:13][CH2:12]1)[OH:10].O>C1COCC1>[CH:11]1([CH:9]([O:10][CH2:4][C:5]([OH:7])=[O:6])[CH3:8])[CH2:13][CH2:12]1

参加物

6

反応物 4

HCID 962WaterHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 791041-Cyclopropylethanol

生成物 1

HCID 221142352-(1-cyclopropylethoxy)Acetic acid収率 29.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a suspension of NaH (80% in oil) (15.7 g, 523 inmol) in THF (180 mL) at 0° C. were added bromoacetic acid (28.0 g, 203 mmol) and a-methylcyclopropane methanol (10.0 g, 116 mmol). The resulting mixture was then stirred at 70° C. After a period of 18 h, the reaction mixture was poured over cold H2O and the H2O phase was extracted once with Et2O. The water phase was acidified with HCl and extracted twice with Et2O. The ether was dried over MgSO4, filtered and evaporated under reduced pressure. The crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH) to provide 5.0 g of the title compound.

後処理

  1. extractionthe H2O phase was extracted once with Et2O
  2. extractionextracted twice with Et2O
  3. dry with materialThe ether was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH)

出典と根拠

ORDレコード
ord-ea01a07f1b7b437c8165fa26e3c444d7
出典データセット
uspto-grants-2000_02
特許番号
US06020343

関連ノート

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