Propargyl bromide → 1-(5-Methylfuran-2-yl)but-3-yn-1-ol

HRID 1032493노트

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HRID 1032493 반응식
[Mg].[CH3:2][C:3]1[O:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[CH2:10](Cl)[C:11]#[CH:12].C(Br)C#C>[Cl-].[Zn+2].[Cl-].C(Cl)C#C.C1(C)C=CC=CC=1.O1CCCC1>[OH:8][CH:7]([C:6]1[O:9][C:3]([CH3:2])=[CH:4][CH:5]=1)[CH2:12][C:11]#[CH:10]

참가 물질

9

반응물 4

HCID 7842Propargyl bromideHCID 120975-MethylfurfuralHCID 122213-Chloro-1-propyneHCID 5462224Magnesium

생성물 1

HCID 98774181-(5-Methylfuran-2-yl)but-3-yn-1-ol수율 86%

시약·촉매·용매 4

HCID 122213-Chloro-1-propyne촉매HCID 3007855Zincchloride촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
10 °C

실험 절차

In the same flask as in Example 1, there were charged granular magnesium (18.2 g), dry zinc chloride (20.4 g) and dry tetrahydrofuran (220 g). Propargyl chloride (0.55 g) was added thereto at 10° C. while stirring. The resultant mixture was kept in an adiabatic condition, whereupon the reaction proceeded. When the heat generation stopped, a mixture of 5-methylfurfural (55.06 g), propargyl chloride (38.6 g), propargyl bromide (11.9 g) and toluene (55 g) was dropwise added to the reaction mixture at 30° C. in 6 hours while stirring under cooling. The resultant mixture was kept at room temperature for 30 minutes while stirring. After completion of the reaction, the reaction mixture was treated in the same manner as in Example 1 to give 2-(1-hydroxy-3-butynyl)-5-methylfuran (64.4 g) in a yield of 86% (based on the starting 5-methylfurfural).

후처리

  1. additionwas dropwise added to the reaction mixture at 30° C. in 6 hours
  2. stirringwhile stirring
  3. temperatureunder cooling
  4. stirringwhile stirring
  5. customAfter completion of the reaction
  6. additionthe reaction mixture was treated in the same manner as in Example 1

출처 및 근거

ORD 기록
ord-e3884370cad6438d8f12fa98b39b1406
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04958033

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