Triethylamine → 4-(Pyridin-2-yl)but-3-ynyl methanesulfonate
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:19][S:20]([O:11][CH2:10][CH2:9][C:8]#[C:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)(=[O:22])=[O:21]Participants
Conditions
- Temperature
- 4 °C
Procedure
To a stirred solution of 4-(pyridin-2-yl)but-3-yn-1-ol (3.60 g, 24 mmol) in dry methylene chloride (30 mL) was added triethylamine (4.40 mL, 32 mmol). The mixture was cooled at 4° C. and methanesulfonyl chloride (2.50 mL, 32 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was then poured over ice/water (100 mL) and stirred for 5 min. To this mixture was added saturated aqueous sodium bicarbonate solution (50 mL) chilled to 4° C., and the mixture was stirred for 30 min, then extracted with DCM. The combined organic fractions were dried over MgSO4, filtered and concentrated under pressure to afford 4.60 g of 4-(pyridin-2-yl)but-3-ynyl methanesulfonate (Yield: 83%) as a brown oil which can be used in the next step without further purification.
Workup
- stirringstirred for 5 min
- temperaturechilled to 4° C.
- stirringthe mixture was stirred for 30 min
- extractionextracted with DCM
- dry with materialThe combined organic fractions were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under pressure
Sources & evidence
- ORD record
- ord-dcee6f831da44389bc50199124635fe8
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883826B2
Reaction notes
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