4-Toluenesulfonyl chloride → HCID 86745999, compound

HRID 654585Notes

Reaction equation

HRID 654585 reaction equation
[OH-:1].[Na+].[S:3](Cl)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1>>[CH3:8][C@H:9]([C@@H:16]([C:15]1[CH:14]=[CH:18][CH:12]=[CH:6][CH:7]=1)[OH:17])[CH2:10][O:4][S:3]([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:1])=[O:5].[S:3]([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)([OH:17])(=[O:5])=[O:4]

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8028Tetrahydrofuran2×HCID 14798Sodium Hydroxide

Product 1

HCID 86745999HCID 86745999, compoundYield 85%

Procedure

To a stirred solution of diol (2S,3S)-2-Methyl-3-phenyl-3-hydroxy-propanol (2.5 g,15 m.mole) in THF (20 ml) was added NaOH (1 g, 40 m.mole) and Tosyl chloride (5 g, 25 m.mole) in THF (5 ml). The cloudy solution was stirred at room temperature for 6 hours and then THF was evaporated under vaccu, diluted with ether (50 ml) washed with water (2×10 ml) and dried over anhydrous MgSO4. Evaporation gave crude tosylate (2S,3S)-2-Methyl-3-phenyl-3-hydroxy-1-tosyloxy-propane (4.1 g, 85%) sufficiently pure for the next step as a yellow viscous oil.

Workup

  1. customTHF was evaporated under vaccu
  2. additiondiluted with ether (50 ml)
  3. washwashed with water (2×10 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation

Sources & evidence

ORD record
ord-814a3762bf5b479c86dcc35144712001
Source dataset
uspto-grants-1992_07
Patent number
US05132457

Reaction notes

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