Dimethyl Sulfoxide → Di(tert-butyl) (4-methylbenzoyl)phosphonate
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([P:20](=[O:31])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.CCN(CC)CC>C(Cl)Cl>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([P:20](=[O:31])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:11])=[CH:14][CH:15]=1Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a solution of oxalyl chloride (1.75 mL) in CH2Cl2 (60 mL) cooled at −78° C. was added DMSO (2.8 mL) dropwise. The mixture was stirred for 10 min at −78° C. and a solution of di(tert-butyl) hydroxy(4-methylphenyl)methylphosphonate (3.14 g in 20 mL of CH2Cl2 was introduced dropwise. After stirring for 30 min at −78° C., 14 mL of Et3N was added. The resulting mixture was stirred for 30 min at −78° C. and 45 min at room temperature, and then quenched with 200 mL of 50% saturated aqueous NaCl solution. The mixture was extracted with 2×200 mL of 1:1 hexane/EtOAc and the extract was dried over MgSO4 and concentrated to give 3 g of the title compound as a yellow oil.
Workup
- stirringAfter stirring for 30 min at −78° C.
- stirringThe resulting mixture was stirred for 30 min at −78° C. and 45 min at room temperature
- customquenched with 200 mL of 50% saturated aqueous NaCl solution
- extractionThe mixture was extracted with 2×200 mL of 1:1 hexane/EtOAc
- dry with materialthe extract was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c314241c127143bf9f47622af200a5a7
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06174874B1
Reaction notes
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