Trityl chloride → HCID 15127968, compound

HRID 2374215Notes

Reaction equation

HRID 2374215 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH2:3][CH3:4].[C:7]1([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>N1C=CC=CC=1.CCOC(C)=O.O>[C:13]([O:6][CH2:1][CH:2]([OH:5])[CH2:3][CH3:4])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 114291,2-Butanediol

Product 1

HCID 15127968HCID 15127968, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1,2-butandiol (2 g) in anh. pyridine (15 mL) was added triphenylmethyl chloride (8 g). The dark reaction mixture was heated at 100° C. for 8 hr and stirred at r.t. for 18 hr. The mixture was then poured in EtOAc/H2O, the phases were separated and the organic layer was washed with sat. aq. NaCl and dried over Na2SO4. The solids were filtered and the solvent evaporated. The residual pyiridine was eliminated by filtration through a pad of silica gel (cHex/EtOAc 8:2). The solvent was evaporated and the residue was purified by flash chromatography (silica gel, cHex/EtOAc 95:5) to give the title compound as a yellow oil (2.67 g).

Workup

  1. customThe dark reaction mixture
  2. customthe phases were separated
  3. washthe organic layer was washed with sat. aq. NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationThe solids were filtered
  6. customthe solvent evaporated
  7. filtrationThe residual pyiridine was eliminated by filtration through a pad of silica gel (cHex/EtOAc 8:2)
  8. customThe solvent was evaporated
  9. customthe residue was purified by flash chromatography (silica gel, cHex/EtOAc 95:5)

Sources & evidence

ORD record
ord-9677cb77e6f64ba8b993f32568088aef
Source dataset
uspto-grants-2008_12
Patent number
US07462622B2

Reaction notes

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