Potassium Hydroxide → HCID 54074160, compound
Reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:14][P:15]([CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)[CH:25]=1)O)(=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:13])([CH3:12])[CH3:11].[OH-].[K+]>ClCCl>[C:10]([O:14][P:15]([CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)[CH:25]=1)[F:7])(=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:13])([CH3:12])[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
Diethylaminosulfur trifluoride (2.2 ml, 8.2 mmol) was dissolved in dichloromethane (25 ml) and the solution was cooled to -70° C. and added dropwise to a solution of the above hydroxymethylphosphonic acid di-tert-butyl ester (4.0 g, 8.3 mmol) in dichloromethane (15 ml) at -70° C. The mixture was stirred at -70° C. for 3 h and at room temperature for 20 h. With stirring the mixture was poured into 1 N aqueous potassium hydroxide (200 ml) and the mixture was extracted with dichloromethane (1×300 ml) and (1×100 ml). The combined organic extracts were washed with saturated aqueous sodium chloride (100 ml), dried (MgSO4), filtered and evaporated in vacuo affording 1.43 g (36%) of ((3-(biphenyl-4-ylmethoxy)-phenyl)fluoromethyl)phosphonic acid di-tert-butyl ester as a solid.
Workup
- stirringWith stirring the mixture
- extractionthe mixture was extracted with dichloromethane (1×300 ml) and (1×100 ml)
- washThe combined organic extracts were washed with saturated aqueous sodium chloride (100 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-64e38f2865804a8e8cb3b8f20151dae6
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080770
Reaction notes
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