4-Toluenesulfonyl chloride → (S)-2-(2,2,4-trimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzene sulfonate

HRID 1896970Notes

Reaction equation

HRID 1896970 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@:5]([CH2:8][CH2:9][OH:10])([CH3:7])[CH2:4][O:3]1.CCN(CC)CC.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:26][C:25]1[CH:27]=[CH:28][C:22]([S:19]([O:10][CH2:9][CH2:8][C@@:5]2([CH3:7])[CH2:4][O:3][C:2]([CH3:11])([CH3:1])[O:6]2)(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11062680(S)-2,2,4-trimethyl-1,3-dioxolan-4-ethanol

Product 1

HCID 13343712(S)-2-(2,2,4-trimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzene sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 4 and Et3N in DCM was added TsCl dropwise. The resulting mixture was stirred at 0° C. for 30 min. The solid was filtered and the solvent was removed. The residue was purified by column chromatography to give compound 5.

Workup

  1. filtrationThe solid was filtered
  2. customthe solvent was removed
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-651cd834aaa743a59b8f4dea8aa7a928
Source dataset
uspto-grants-2013_08
Patent number
US08518984B2

Reaction notes

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