Methanol → HCID 7784447, compound

HRID 1742519Notes

Reaction equation

HRID 1742519 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[CH2-:5][C:6]([CH3:8])=O.O=[CH:10][C@@H:11]([C@@H:13]([C@@H:15]([C@@H:17]([CH2:19][OH:20])[OH:18])[OH:16])[OH:14])[OH:12].[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CO>C1COCC1.CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH3:1][C:2]1([CH3:4])[O:12][C@@H:11]([C@H:13]2[O:14][C@@H:19]3[O:20][C:6]([CH3:8])([CH3:5])[O:18][C@@H:17]3[C@@H:15]2[O:16][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][O:3]1

Participants

8

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178521084HCID 178521084, compound

Product 1

HCID 7784447HCID 7784447, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a stirred solution of the allose diacetonide 2 (19.6 g, ca. 75 mmol) in THF-DMF (500 mL, 4:1 v/v) at 0° C. and under argon was added a 60% sodium hydride dispersion in mineral oil (6.0 g, 150 mmol) portionwise over 30 min. The resulting mixture was allowed to warm to room temperature over 1 h, then it was re, cooled to 0° C. before benzyl bromide (25.7 g, 17.9 mL, 150 mmol) and tetra-n-butlyammonium iodide (1.0 g) were added. The resulting mixture was allowed to warm to room temperature and stir for 16 h. The reaction mixture was cooled to 0° C. and anhydrous methanol (20 mL) was cautiously added over 30 min. The resulting mixture was allowed to warm to room temperature and stir for 1 h before the THF was removed by rotary evaporation. The residue was suspended in H2O (250 mL) and extracted with ethyl acetate (4×200 mL). The combined organic fractions were washed with H2O (500 mL) and brine (200 mL), dried over Na2SO4, filtered, and concentrated to a clear, yellow oil (46.8 g crude). This material was used without further purification. ##STR66##

Workup

  1. additionwere added
  2. temperatureto warm to room temperature
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. temperatureto warm to room temperature
  5. customwas removed by rotary evaporation
  6. extractionextracted with ethyl acetate (4×200 mL)
  7. washThe combined organic fractions were washed with H2O (500 mL) and brine (200 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to a clear, yellow oil (46.8 g crude)
  11. customThis material was used without further purification

Sources & evidence

ORD record
ord-c4f901691d864bb08fa014de0067052b
Source dataset
uspto-grants-1994_08
Patent number
US05338865

Reaction notes

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