Ethanol → HCID 67930810, compound

HRID 728210Notes

Reaction equation

HRID 728210 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 110352621,6-Anhydro-2,4-bis-O-(phenylmethyl)-β-D-glucopyranose

Product 1

HCID 67930810HCID 67930810, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose (Chem Ber 70 (1937) 1848-1856) (1.5 g, 4.4 mmol) and a trace of tetrabutylammonium iodide in tetrahydrofuran (10 ml) was stirred with sodium hydride (60% dispersion in oil, 200 mg, 5 mmol). Methyl iodide (0.7 g, 5 mmol) was added. The reaction was complete almost immediately (t.l.c evidence). Ethanol was added to the reaction mixture to destroy excess sodium hydride. The mixture was diluted with chloroform and washed with water and brine. The organic phase was dried and evaporated and the residue was chromatographed on silica gel (hexane/ethyl acetate, 2:1) to give the title compound (1.7 g, 109%), as a colourless syrup that yellowed on standing [α]D -33.5°. 13C Nmr peaks were recorded at 100.5 (C-1), 76.6 (C-2), 79.0 (C-3), 76.1 (C-4), 74.3 (C-5), 65.3 (C-6), 71.9 and 71.2 (PhCH2O), 58.0 (OCH3), and 138.0, 137.9, 128.4, 127.9 and 127.8 (aromatic).

Workup

  1. customto destroy excess sodium hydride
  2. additionThe mixture was diluted with chloroform
  3. washwashed with water and brine
  4. customThe organic phase was dried
  5. customevaporated
  6. customthe residue was chromatographed on silica gel (hexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-1445fc28850446fb8a980dc0a5ee36ad
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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