Aluminium lithium hydride → Diaza-18-crown-6

HRID 1658906노트

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HRID 1658906 반응식
O=[C:2]1[CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][C:13](=O)[NH:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[O:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:2][NH:3][CH2:4][CH2:5]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 213163171,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-6,17-dione

생성물 1

HCID 72805Diaza-18-crown-6수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 18.5 g. of the diamide obtained in Example 3 in 450 ml. anhydrous tetrahydrofurane is slowly added to a mixture of 150 ml. anhydrous tetrahydrofurane and 12 g. LiAlH4 while stirring and heating at the reflux temperature. After the addition is completed, the mixture is stirred under reflux and under a nitrogen atmosphere for 24 hours. After cooling to room temperature the excess reagent is destroyed by adding a mixture of water and THF (1:2). The mixture is filtered and the filtrate is evaporated to dryness. The residue is dissolved in benzene and the solution is passed through a column of Al2O3 with benzene as eluant. The solution is evaporated to dryness and after recrystallization from benzene/petrol ether 13.5 g. of the desired product is obtained. m.p. = 115°C-116°C.

후처리

  1. temperatureheating at the reflux temperature
  2. additionAfter the addition
  3. temperatureunder reflux and under a nitrogen atmosphere for 24 hours
  4. customis destroyed
  5. additionby adding
  6. additiona mixture of water and THF (1:2)
  7. filtrationThe mixture is filtered
  8. customthe filtrate is evaporated to dryness
  9. dissolutionThe residue is dissolved in benzene
  10. customThe solution is evaporated to dryness
  11. customafter recrystallization from benzene/petrol ether 13.5 g

출처 및 근거

ORD 기록
ord-e6bcab5e5a57446aadbe5b840c6951c1
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03966766

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