Dichloromethane → HCID 15389966, compound

HRID 1707946Notes

Reaction equation

HRID 1707946 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][O:5][C@H:6]1[C@@H:12]([CH2:13][CH3:14])[O:11][CH:8](OC)[C@@H:7]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1.[Sn](Cl)(Cl)(Cl)Cl.ClCCl.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:13]([C@H:12]1[O:11][C@H:8]2[C@H:7]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][C:22]=32)[C@H:6]1[O:5][CH2:4][C:3]1[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=1[F:1])[CH3:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 15389968HCID 15389968, compound

Product 1

HCID 15389966HCID 15389966, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.62 g of methyl 5-deoxy-3-O-(2-fluorobenzyl)-5-C- methyl-2-O-(3-methylbenzyl)-D-xylofuranoside (a mixture of alpha and beta forms) obtained in 1) was dissolved in 10 ml of acetonitrile and 4.97 ml of tin tetrachloride (a 1.0 M dichloromethane solution) were added under cooling with ice. The resulting mixture was stirred at room temperature for 3 hours and then poured into a saturated aqueous sodium hydrogen carbonate solution with ice. The organic phase was thoroughly washed with water and then dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain an oily product. The crude product was purified by silica gel chromatography (developing solvent: n-hexane:ethyl acetate=5:1) and 0.39 g of the target compound was obtained. (Yield: 68.4%)

Workup

  1. customobtained in 1)
  2. temperatureunder cooling with ice
  3. washThe organic phase was thoroughly washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto obtain an oily product
  7. customThe crude product was purified by silica gel chromatography (developing solvent: n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-c805b0b9d8d04ff8817f908f75869b18
Source dataset
uspto-grants-1994_10
Patent number
US05356866

Reaction notes

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