Triethylamine → Phosphonium, [[5-(4-fluorophenyl)-2-oxazolyl]methyl]triphenyl-, chloride (1:1)
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH2:13]O)=[N:10][CH:9]=2)=[CH:4][CH:3]=1.CCN(CC)CC.O=S(Cl)[Cl:24].C([O-])([O-])=O.[Na+].[Na+].[C:32]1([P:38]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[Cl-:24].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH2:13][P+:38]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[N:10][CH:9]=2)=[CH:4][CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
[5-(4-fluorophenyl)-1,3-oxazol-2-yl]methanol (0.46 g, 2.4 mmol) was dissolved in DCM (5 ml), then Et3N (0.3 ml, 2.4 mmol) and SOCl2 (0.35 ml,4.7 mmol) were added. The reaction mixture was stirred for 1 hour at room temperature under nitrogen. The mixture was diluted with DCM (20 ml) and a saturated solution of Na2CO3 (20 ml) was added carefully. The organic layer was separated, washed with brine (20 ml), dried over MgSO4 and concentrated in vacuo to give a yellow oil. This oil (0.5 g, 2.38 mmol) was treated with an equimolar amount of triphenylphosphine as described for Intermediate A (Step 3) to give the title compound. δH (360 MHz, DMSO) 5.76 (2H, d, J 16.0), 7.29 (2H, t, J 7.0), 7.39-7.46 (2H, m), 7.61 (1H, s), 7.74-7.95 (15H, m).
Workup
- customThe organic layer was separated
- washwashed with brine (20 ml)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customto give a yellow oil
Sources & evidence
- ORD record
- ord-186f9baea74b473194e7e7f8283930d5
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07452899B2
Reaction notes
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