Hydrochloric Acid → Toluene-4-sulfonic acid 2-cyclopropoxy-ethyl ester

HRID 2403744Notes

Reaction equation

HRID 2403744 reaction equation
[CH:1]1([O:4][CH2:5][CH2:6][OH:7])[CH2:3][CH2:2]1.[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9].CCN(CC)CC.Cl>>[CH3:15][C:14]1[CH:16]=[CH:17][C:11]([S:8]([O:7][CH2:6][CH2:5][O:4][CH:1]2[CH2:3][CH2:2]2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 120233832-cyclopropoxyethanol

Product 1

HCID 59557773Toluene-4-sulfonic acid 2-cyclopropoxy-ethyl ester

Procedure

To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil.

Workup

  1. extractionthe reaction was extracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. customThe oil was purified by preparative TLC
  7. customto obtain intermediate BP (50 mg) as a yellow oil

Sources & evidence

ORD record
ord-89f69e0f80414f7f81600e2266bade75
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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