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

HRID 1524619Notes

Reaction equation

HRID 1524619 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-eb11d254e5734bd2814ad87c9eff6fd2
Source dataset
uspto-grants-2015_07
Patent number
US09079913B2

Reaction notes

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