Triethylamine → (6Z,15Z)-henicosa-6,15-dien-11-yl methanesulfonate
Reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH:11]([OH:22])[CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH3:30][S:31]([O:22][CH:11]([CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:9][CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])(=[O:33])=[O:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cooled solution (0° C.) of 6Z,15Z)-henicosa-6,15-dien-11-ol 4 (5.6 g, 18.2 mmol) and triethylamine (3.8 mL, 27.2 mmol) in anhydrous dichloromethane (50 mL) was slowly added methanesulfonyl chloride (2.1 mL, 27.2 mmol). The reaction mixture was stirred for 2 hours at room temperature then diluted with dichloromethane (50 mL). The solution was washed with saturated sodium bicarbonate (3×25 mL) then the combined aqueous washes were extracted with dichloromethane (50 mL). The combined dichloromethane extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The pale yellow oil was filtered through a pad of silica (100% DCM) to afford (6Z,15Z)-henicosa-6,15-dien-11-yl methanesulfonate 5 as a crude colorless oil (7.6 g). Rf 0.8 (100% CH2Cl2).
Workup
- customTo a cooled solution (0° C.) of 6Z,15Z
- washThe solution was washed with saturated sodium bicarbonate (3×25 mL)
- extractionthe combined aqueous washes were extracted with dichloromethane (50 mL)
- dry with materialThe combined dichloromethane extracts were dried on magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo to dryness
- filtrationThe pale yellow oil was filtered through a pad of silica (100% DCM)
Sources & evidence
- ORD record
- ord-6b816c51d70c4d6d958e9729e59b8ac3
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09352042B2
Reaction notes
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