Hexane → 5-(t-Butyldimethylsilyloxy)methyl-2-hydroxymethylfuran

HRID 609777

반응식

HRID 609777 반응식
CCCCCC.[H-].[Na+].[O:9]1[C:13]([CH2:14][OH:15])=[CH:12][CH:11]=[C:10]1[CH2:16][OH:17].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(OCC)C.O1CCCC1>[Si:18]([O:15][CH2:14][C:13]1[O:9][C:10]([CH2:16][OH:17])=[CH:11][CH:12]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 746632,5-Furandimethanol

생성물 1

HCID 121775085-(t-Butyldimethylsilyloxy)methyl-2-hydroxymethylfuran

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

According to the method of P. G. McDougal, et al., J. Org. Chem., 51, 3388-3390 (1986), combine hexane washed sodium hydride (20 mmol) and tetrahydrofuran (40 mL). Slowly add 2,5-furandimethanol (20 mmol). After gas evolution ceases, add t-butyldimethylsilyl chloride (20 mmol) and stir vigorously. After about 1 hour, pour the reaction mixture into diethyl ether and extract with a saturated aqueous solution of sodium carbonate, water, and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 5-(t-butyldimethylsilyloxy)methyl-2-hydroxymethylfuran. Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine (10 mmol), 5-(t-butyldimethylsilyloxy)-methyl-2-hydroxymethylfuran (10 mmol), and triphenylphosphine (10 mmol) in tetrahydrofuran (100 mL). Add diethyl azodicarboxylate (10 mmol). After 18 hours, evaporate the reaction mixture in vacuo to give a residue. Partition the residue between ethyl acetate and water. Separate the organic layer and extract with water and brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel to give 1-(t-butoxycarbonyl)-4-(1-(5-(t-butyldimethylsilyloxy)-methylfur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine.

후처리

  1. extractionextract with a saturated aqueous solution of sodium carbonate, water
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-d6bb7727c0364e56be6a0667580f5ac1
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998439

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