Acetic Acid → Ethyl 2-(furan-2-yl)-2-hydroxyacetate

HRID 253985ノート

反応式

HRID 253985 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 74230Ethyl alpha-oxofuran-2-acetateHCID 4311764Sodium borohydride

生成物 1

HCID 11446571Ethyl 2-(furan-2-yl)-2-hydroxyacetate収率 71%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

Ethyl 2-(furan-2-yl)-2-oxoacetate (15.5 g, 92.1 mmol) in ethanol (500 mL) and water (25 mL) at 0° C. was treated with sodium borohydride (1.74 g, 46.05 mmol). The mixture was stirred for 15 minutes, at which point acetic acid (10 mL) was slowly added. After the cessation of gas evolution, water (100 mL) was carefully added, and the reaction mixture was concentrated. The residue was dissolved in methylene chloride and washed with brine. The crude product was dried and concentrated to give ethyl 2-(furan-2-yl)-2-hydroxyacetate as a pale brown viscous oil (11.05 g, 71%) which was used without further purification.

後処理

  1. additionwas slowly added
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with brine
  5. dry with materialThe crude product was dried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-2ce8e42a330b45c585caf3acaef195c9
出典データセット
uspto-grants-2011_01
特許番号
US07872031B2

反応ノート

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