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

HRID 2038498Notes

Reaction equation

HRID 2038498 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>C(Cl)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

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) in 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-f25a8c3801cf4a2a94df72ac3cb4e15b
Source dataset
uspto-grants-2013_11
Patent number
US08575321B2

Reaction notes

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