Methanol → 1,2,3-Propanetriol, 2-methyl-, 1-(4-methylbenzenesulfonate), (R)-

HRID 1974674Notes

Reaction equation

HRID 1974674 reaction equation
[S:1]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)([O:4][CH2:5][C@@:6]1([CH3:16])[CH2:10][O:9]C2(CCCCC2)[O:7]1)(=[O:3])=[O:2].CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[S:1]([C:17]1[CH:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=1)([O:4][CH2:5][C@@:6]([OH:7])([CH3:16])[CH2:10][OH:9])(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 18653128HCID 18653128, compound

Product 1

HCID 545537721,2,3-Propanetriol, 2-methyl-, 1-(4-methylbenzenesulfonate), (R)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.22 g (6.52 mmol) of {(R)-2-methyl-1,4-dioxaspiro[4,5]dec-2-yl}methyl tosylate are repeatedly evaporated from methanol in the presence of a catalytic amount of p-toluenesulfonic acid and the residue is finally purified by chromatography over silica gel 60 (0.040-0.063 mm, 55 g) using diethyl ether/methylene chloride (1:2) as the eluent. There are obtained 829 mg (3.18 mmol, 49% of the theoretical yield) of (R)-2,3-dihydroxy-2-methylpropyl tosylate, 98% pure by gas chromatography, [α]365 =-19.9° (1% in CHCl3).

Workup

  1. customthe residue is finally purified by chromatography over silica gel 60 (0.040-0.063 mm, 55 g)
  2. customThere are obtained 829 mg (3.18 mmol, 49% of the

Sources & evidence

ORD record
ord-4d67cd079802428c86f816972d0fa24d
Source dataset
uspto-grants-1994_02
Patent number
US05283346

Reaction notes

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