Water → HCID 67930806, compound

HRID 728218Notes

Reaction equation

HRID 728218 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@H:11]([O:17][CH3:18])[C@@H:10]1[OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH3:22]I.O>CS(C)=O>[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@H:11]([O:17][CH3:18])[C@@H:10]1[O:19][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 67930814HCID 67930814, compound

Product 1

HCID 67930806HCID 67930806, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,6-Anhydro-4-O-benzyl-2-O-methyl-β-D-allopyranose (0.135 g) (see Example 29) was dissolved in dimethylsulphoxide (0.5 ml) and stirred with powdered potassium hydroxide (0.118 g). Methyl iodide (0.568 g) was added in two portions, and the reaction mixture was left overnight at room temperature. Water (10 ml) was added and the mixture was extracted with chloroform (3×10 ml). The combined extracts were washed with brine, filtered through Whatman 1PS paper, and evaporated to a red oil. This was subjected to preparative t.l.c. on silica gel eluted with ethyl acetate/hexane, 1:1, to yield the title compound as a colourless syrup (0.073 g); 1H-nmr data: 7.2-7.5 (m, Ph), 5.6 (d, H-1), 4.8 (m, PhCH2O), 4.55 (m, H-5), 3.3-3.7 (m, H-2,3,4,6,6'), and 3.40 and 3.57 (s, OMe).

Workup

  1. extractionthe mixture was extracted with chloroform (3×10 ml)
  2. washThe combined extracts were washed with brine
  3. filtrationfiltered through Whatman 1PS paper
  4. customevaporated to a red oil
  5. washon silica gel eluted with ethyl acetate/hexane, 1:1

Sources & evidence

ORD record
ord-c59aca57e5a64c7cb128a5d499e0ebe2
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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