Citric Acid → 5-(Hydroxymethyl)furan-2-carbonitrile

HRID 1952850

반응식

HRID 1952850 반응식
[BH4-].[Na+].[C:3]([C:5]1[O:9][C:8]([CH:10]=[O:11])=[CH:7][CH:6]=1)#[N:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[OH:11][CH2:10][C:8]1[O:9][C:5]([C:3]#[N:4])=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 311Citric AcidHCID 6421395-Cyano-2-furaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 30214065-(Hydroxymethyl)furan-2-carbonitrile수율 8,800%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
-30 °C

실험 절차

2.34 g (62 mmol) of sodium borohydride were added in portions to a solution of 30 g (0.25 mol) of 5-cyanofuran-2-carbaldehyde in 500 ml of absolute ethanol at -30° C. The solution was stirred at -30° C. for 2 hours and, while cooling, was adjusted to pH 7 with a 5% strength citric acid solution in water. The reaction mixture was concentrated under water pump vacuum, saturated sodium chloride solution was added to the residue, the mixture was extracted several times with 150 ml of diethyl ether each time, the combined organic phases were dried over magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under water pump vacuum at room temperature. This resulted in 27 g (22 mol, 88%) of the title compound as a dark red oil, which was employed without further purification in the following reactions. 1H-NMR (250 MHz, d6 -DMSO): δ=4.4 (m, 2H), 5.6 (bs, 1H), 6.6 (d, 1H), 7.5 (d, 1H).

후처리

  1. temperaturewhile cooling
  2. concentrationThe reaction mixture was concentrated under water pump vacuum, saturated sodium chloride solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted several times with 150 ml of diethyl ether each time
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. filtrationthe desiccant was filtered off
  7. distillationthe solvent was distilled off under water
  8. customat room temperature

출처 및 근거

ORD 기록
ord-595a70d2fddd4cb0852a24aab3c4685d
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06114358

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