4-Toluenesulfonyl chloride → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

HRID 1012644Notes

Reaction equation

HRID 1012644 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:4][O:3]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7528SolketalHCID 8471Triethylamine

Product 1

HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolan (3.96 g, 30 mmol) and triethyl amine (5 mL) were dissolved in CH2Cl2 (50 mL). p-Toluenesulphonyl chloride (3.8 g, 20 mmol) was added. The solution was stirred for 3 h after which 4-dimethylaminopyridine (0.05 g, 0.04 mmol) was added. The solution was stirred for 0.5 h after which the solution was concentrated in vacuo. The residue was taken up in CH2Cl2 and the organic phase was washed with H2O, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford the title compound.

Workup

  1. additionwas added
  2. concentrationwas concentrated in vacuo
  3. washthe organic phase was washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6c62f9f40f6141619ab6dfa1fede4b90
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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