Water → HCID 2733809, compound

HRID 2300155Notes

Reaction equation

HRID 2300155 reaction equation
[OH:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.[C:9](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>N1C=CC=CC=1>[C:9]([O:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 2733813(S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone

Product 1

HCID 2733809HCID 2733809, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

105.5 g of (5S)-5-(hydroxymethyl)tetrahydro-2-furanone was dissolved in 1.2 L pyridine, and 380 g of trityl chloride was added thereto at room temperature, and the mixture was stirred at 80° C. overnight. After the reaction was completed, the mixture was cooled, water was added thereto, extracted with ethyl acetate, and then washed with brine. The solvent was removed, and the resulting residue was dissolved in 300 ml chloroform, and after 600 ml silica gel was added thereto, the solvent was removed. The resulting residue was purified by silica gel column chromatography to give 149.3 g of (5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone.

Workup

  1. temperaturethe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customThe solvent was removed
  5. dissolutionthe resulting residue was dissolved in 300 ml chloroform
  6. additionafter 600 ml silica gel was added
  7. customthe solvent was removed
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c26aaa6d62f849cea1deee44b7f7cea8
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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