4-Toluenesulfonyl chloride → HCID 54277958, compound

HRID 892811Notes

Reaction equation

HRID 892811 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@@H:8]([CH:12]([CH3:14])[CH3:13])[C@@:7]([CH2:16][CH2:17][OH:18])([OH:15])[CH2:6][CH2:5]2.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:18][CH2:17][CH2:16][C@:7]2([OH:15])[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=3)[C@H:8]2[CH:12]([CH3:13])[CH3:14])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67917369HCID 67917369, compound

Product 1

HCID 54277958HCID 54277958, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

28.5 g (0.113 mol) of [1R,2R]-(-)-2-[6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl]ethanol were dissolved in 150 ml of pyridine and treated portionwise within 30 minutes at 0° with 31.5 g (0.165 mol) of p-toluenesulphonyl chloride. After 90 minutes the reaction solution was poured into ice-water and extracted with ether. The organic phase was washed in succession with 3N hydrochloric acid, water and a saturated sodium carbonate solution. After drying over magnesium sulphate and evaporation of the solvent under reduced pressure, the remaining oily residue was recrystallized from ether/hexane, yielding 38.8 g (85%) of [1R,2R]-(-)-2-[6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl]ethyl p-toluenesulphonate as white crystals, m.p. 65°-67°; [α]D20 =-54.1° (c=1, methanol).

Workup

  1. extractionextracted with ether
  2. washThe organic phase was washed in succession with 3N hydrochloric acid, water
  3. dry with materialAfter drying over magnesium sulphate and evaporation of the solvent under reduced pressure
  4. customthe remaining oily residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-f65dd1dc1b794be7b014b8f144fc3c9f
Source dataset
uspto-grants-1992_06
Patent number
US05120759

Reaction notes

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