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Triethylamine → 2-(1-Hydroxycyclopropyl)ethyl methanesulfonate

HRID 1517863
Notes
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Reaction equation

HRID 1517863 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:7])[CH2:6][CH2:5]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:1][CH2:2][CH2:3][C:4]1([OH:7])[CH2:6][CH2:5]1)(=[O:18])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 133068711-(2-Hydroxyethyl)cyclopropan-1-ol

Product 1

HCID 866407922-(1-Hydroxycyclopropyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

A mixture of 1-(2-hydroxyethyl)cyclopropanol (310 mg, 3.04 mmol) and triethylamine (614.1 mg, 6.08 mmol) in 10 mL of dichloromethane was stirred at −10° C. for 30 min. Methanesulfonyl chloride (348 mg, 3.04 mmol) was added via a syringe. After stirring at −10° C. for 1 hr, the reaction mixture was quenched with ice-water (2 mL) and extracted with dichloromethane (20 mL×4). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give yellow oil (used for the next step quickly).

Workup

  1. stirringAfter stirring at −10° C. for 1 hr
  2. customthe reaction mixture was quenched with ice-water (2 mL)
  3. extractionextracted with dichloromethane (20 mL×4)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give yellow oil (

Sources & evidence

ORD record
ord-1b71481da4df4d14be75da6cb994ad10
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232294B2

Reaction notes

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