2-Fluoroethanol → HCID 53853967, compound

HRID 343870Notes

Reaction equation

HRID 343870 reaction equation
[F:1][CH2:2][CH2:3][OH:4].O[CH:6]1[C:15]2[C:10](=[C:11]([F:22])[CH:12]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:14]=2[Cl:16])[S:9][CH2:8][CH2:7]1>S(=O)(=O)(O)O>[F:1][CH2:2][CH2:3][O:4][CH:6]1[C:15]2[C:10](=[C:11]([F:22])[CH:12]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:14]=2[Cl:16])[S:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 97372-FluoroethanolHCID 54407823HCID 54407823, compound

Product 1

HCID 53853967HCID 53853967, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

5 ml of 2-fluoroethanol and 3 drops of concentrated sulfuric acid were added to 2.4 g (8.2 mmol) of 4-hydroxy-5-chloro-6-ethoxycarbonyl-8-flurothiochroman (corresponding to compound of the formula (IX)), and the mixture was refluxed under heat for 5 hours. After allowed to cool, the reaction mixture was poured into an ice bath, and extracted with ethyl acetate twice. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 2.2 g (yield 79%) of 4-(2-fluoroethoxy)-5-chloro-6-ethoxycarbonyl-8-fluorothiochroman (corresponding to compound of the formula (X)).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heat for 5 hours
  3. temperatureto cool
  4. additionthe reaction mixture was poured into an ice bath
  5. extractionextracted with ethyl acetate twice
  6. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-24c891ae0a0d4abc86b8ddbe25149db0
Source dataset
uspto-grants-1999_01
Patent number
US05863866

Reaction notes

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