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

HRID 2253563Notes

Reaction equation

HRID 2253563 reaction equation
[S:1]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)([O:4][CH2:5][C@@:6]1([CH3:13])[CH2:10][O:9]C(C)(C)[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:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=1)([O:4][CH2:5][C@@:6]([OH:7])([CH3:13])[CH2:10][OH:9])(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 54135429HCID 54135429, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.42 g (4.74 mmol) of {(R)-2,2,4-trimethyl-1,3-dioxolan-4-yl}methyl tosylate are evaporated twice from 100 ml of methanol in the presence of a catalytic amount of p-toluenesulfonic acid at 16 mbar/40° C. and the residue is finally purified by chromatography over silica gel 60 (0.040-0.063 mm, 20 g) using methylene chloride/diethyl ether (1:1) as the eluent. There are obtained 907 mg (3.49 mmol, 74% of the theoretical yield) of (R)-2,3-dihydroxy-2-methylpropyl tosylate, 99% pure by gas chromatography, [α]365 =-19.0° (1% in CHCl3).

Workup

  1. customthe residue is finally purified by chromatography over silica gel 60 (0.040-0.063 mm, 20 g)
  2. customThere are obtained 907 mg (3.49 mmol, 74% of the

Sources & evidence

ORD record
ord-9923abbfc0854623b05cc1b2ed1d95cc
Source dataset
uspto-grants-1993_08
Patent number
US05232852

Reaction notes

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