Dimethyl Sulfoxide → HCID 86605055, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:14]([CH3:30])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13]1.CCN(CC)CC>C(Cl)Cl>[CH3:30][C:14]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][C:12](=[O:11])[CH2:16][N:15]1[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a flame-dried flask equipped with stir bar under nitrogen was charged anhydrous CH2Cl2 (5 mL). The flask was immersed in a cooling bath at −78° C. Oxalyl chloride (0.24 mL, 2.7 mmol) was added neat followed by DMSO (0.29 mL, 4.1 mmol) dropwise. The reaction was stirred 10 minutes at −78° C. prior to the addition of alcohol 20-5 (0.19 g, 0.7 mmol) in minimal CH2Cl2. The resulting solution was stirred an additional 1 hour at −78° C. prior to the addition of Et3N (0.76 mL, 5.4 mmol) neat and dropwise. The reaction warmed to 0° C. over 2 hour. Upon completion, the reaction solution was washed with 5% aq. NaHCO3, dried (MgSO4), filtered and concentrated. The residue was carried crude into the vinyl triflate formation: LRMS m/z (M-C(CH3)3+H) 220.1 found, 220.2 required.
Workup
- customTo a flame-dried flask equipped
- customThe flask was immersed in a cooling bath at −78° C
- stirringThe reaction was stirred 10 minutes at −78° C.
- stirringThe resulting solution was stirred an additional 1 hour at −78° C.
- washUpon completion, the reaction solution was washed with 5% aq. NaHCO3
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6bf27debe649470591970e15149f714d
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348440B2
Reaction notes
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