1,2-Dichloroethane → HCID 13832665, compound

HRID 457481Notes

Reaction equation

HRID 457481 reaction equation
[O:1]=[CH:2][C@@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].Cl[CH2:12]CCl>C(Cl)Cl>[CH3:12][O:1][CH2:2][C@H:3]1[O:4][CH:9]([OH:10])[C@H:7]([OH:8])[C@@H:5]1[OH:6]

Participants

4

Reactant 2

HCID 111,2-Dichloroethane3×HCID 5311110Aldehydo-D-ribose

Product 1

HCID 13832665HCID 13832665, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Vorbr□ggen coupling To the appropriate silylated base (12.9 mmol) was added the appropriate ribose (10.3 mmol) in 15 ml dry 1,2-dichloroethane. The residue was co-evaporated twice with dry 1,2-dichloroethane and subsequently dissolved in 75 ml dry 1,2-dichloroethane. The solution was gently refluxed and after 5 minutes trimethylsilyl-trifluoromethane sulfonate (TMS triflate) (997 □l, 5.16 mmol) was added. The mixture was refluxed for 2 hr, cooled to room temperature and diluted with CH2Cl2. It was extracted with 5% NaHCO3 and water. The organic layer was dried (MgSO4), concentrated and purified by column chromatography.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 2 hr
  3. extractionIt was extracted with 5% NaHCO3 and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-2fb45dfab51947368a12ab5314b1fbac
Source dataset
uspto-grants-2007_03
Patent number
US07189706B2

Reaction notes

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