Ethanol → HCID 67930784, compound

HRID 728215Notes

Reaction equation

HRID 728215 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]([OH:15])[C@H:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:12]2[CH2:24][O:25][C@@H:10]1[O:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.[CH2:30](O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:1]([O:8][C@@H:9]1[C@H:14]([O:15][CH3:30])[C@H:13]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:12]2[CH2:24][O:25][C@@H:10]1[O:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67930763HCID 67930763, compound

Product 1

HCID 67930784HCID 67930784, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,6-anhydro-2,4-di-O-benzyl-β-D-allopyranose (Example 20) (1 g, 2.9 mmol), sodium hydride (60%, 200 mg, 5 mmol), methyl iodide (excess) and tetrabutylammonium iodide (trace) in tetrahydrofuran was stirred overnight at room temperature. Ethanol was added to destroy excess sodium hydride and the solution evaporated to near dryness. The residue was taken up in dichloromethane and washed with water and brine. The organic phase was dried (Na2SO4) and evaporated, and the residue was chromatographed on silica gel (hexane/ethyl acetate, 1:1) to give the title compound as a colourless syrup (800 mg, 77%), [α]D -53.6°; 13C-nmr data: 128.2, 128.0, 127.9 (aromatic), 100.5 (C-1), 74.6 and 74.1 (C-2 and C-4), 73.6 (OCH2Ph), 73.5 and 73.1 (C-3 and C-5), 72.2 (OCH2Ph), 64.8 (C-6), and 56.8 (OCH3).

Workup

  1. customto destroy excess sodium hydride
  2. customthe solution evaporated
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customthe residue was chromatographed on silica gel (hexane/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-6ce4236f5d5f40ff82c7ee96e0180eb2
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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