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

HRID 379444

Reaction equation

HRID 379444 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to the method of P. G. McDougal, et al., J. Org. Chem., 5, 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.

Workup

  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

Sources & evidence

ORD record
ord-c92ec0e53361469f866460f5499e7347
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Linked notes

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