Pyridine → HCID 10970327, compound

HRID 1383630Notes

Reaction equation

HRID 1383630 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[CH:5]=[CH:4]1.N1C=CC=CC=1.[C:15]1([C:21](Cl)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:15]1([C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:1][CH2:2][C@@H:3]2[O:7][C:6](=[O:8])[CH:5]=[CH:4]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 27250005-(Hydroxymethyl)furan-2(5H)-one

Product 1

HCID 10970327HCID 10970327, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-(+)-5-Hydroxymethyl-2 (5H)-furanone (1.94 g, 17.0 mmol) was dissolved in anhydrous pyridine (60 mol), triphenylmethyl chloride (14.3 g, 51.2 mmol) was added to the solution at room temperature, and the mixture was stirred for 6 hr. Ethanol was added to the reaction solution at 0° C., and the mixture was stirred for one hr. The reaction solution was concentrated under reduced pressure, and the concentrate was subjected to azeotropic distillation twice with toluene and purified by column chromatographic separation on silica gel (hexane:ethyl acetate=3:1 to 2:1) to give (R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone (5.47 g, 90%).

Workup

  1. stirringthe mixture was stirred for one hr
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. distillationthe concentrate was subjected to azeotropic distillation twice with toluene
  4. custompurified by column chromatographic separation on silica gel (hexane:ethyl acetate=3:1 to 2:1)

Sources & evidence

ORD record
ord-3d9cef832c3547f9a6d63876fcffbf2f
Source dataset
uspto-grants-2001_07
Patent number
US06255339B1

Reaction notes

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