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

HRID 253985노트

반응식

HRID 253985 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 11446571Ethyl 2-(furan-2-yl)-2-hydroxyacetate수율 71%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ce8e42a330b45c585caf3acaef195c9
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872031B2

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