Water → 2,2-Diisoamyl-4,6-di-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 1376990노트

반응식

HRID 1376990 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:13][C:14]2[O:18][C:17]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][C:15]=2[C:29]=1[C:30]([CH3:33])([CH3:32])[CH3:31])(=O)C.O.[Cl-].[NH4+]>O1CCCC1>[CH2:24]([C:17]1([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][C:15]2[C:29]([C:30]([CH3:33])([CH3:32])[CH3:31])=[C:11]([OH:10])[C:12]([C:34]([CH3:35])([CH3:36])[CH3:37])=[CH:13][C:14]=2[O:18]1)[CH2:25][CH:26]([CH3:28])[CH3:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 111128205-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuranHCID 21226445Aluminium lithium hydride

생성물 1

HCID 110473792,2-Diisoamyl-4,6-di-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran수율 57.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium aluminum hydride (1.90 g) was suspended in tetrahydrofuran (200 ml) under a nitrogen atmosphere. A solution of 5-acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran (17.4 g) in tetrahydrofuran (60 ml) was added dropwise to the suspension under cooling with ice. After heating under reflux overnight, the mixture was cooled to room temperature and water and a saturated aqueous solution of ammonium chloride were added in that order. The resulting insolubles were filtered off on Celite. The filtrate was subjected to extraction with diethyl ether, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by silica gel chromatography (n-hexane) to afford 2,2-diisoamyl-4,6-di-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran [9.0 g (yield, 57%)] as a colorless oil.

후처리

  1. temperatureunder cooling with ice
  2. temperatureAfter heating
  3. temperatureunder reflux overnight
  4. filtrationThe resulting insolubles were filtered off on Celite
  5. extractionThe filtrate was subjected to extraction with diethyl ether
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel chromatography (n-hexane)

출처 및 근거

ORD 기록
ord-4900916a18d64b47b77473f4064758c2
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663373

반응 노트

불러오는 중…