Water → 5-Cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid
Reaction equation
[CH2:1]([O:3][P:4]([CH:9]([C:21]#[N:22])[CH:10]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH2:11][CH2:12][CH:13]=C)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[O-:23][Mn](=O)(=O)=O.[K+].OS([O-])=O.[Na+].[OH2:34]>ClCCl.C(O)(=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:21]([CH:9]([P:4]([O:5][CH2:6][CH3:7])([O:3][CH2:1][CH3:2])=[O:8])[CH:10]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH2:11][CH2:12][C:13]([OH:23])=[O:34])#[N:22]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of [1-cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester (6.26 g, 19.0 mmol) in dichloromethane (211 mL), H2O (173 mL) and acetic acid (73 mL), was added tetrabutylammonium bromide (127 mg) followed by the portionwise addition of KMnO4. The resulting mixture was then stirred at room temperature overnight. The resulting viscous solution was cooled to 0° C., and NaHSO3 was added slowly until the mixture became clear. The layers were separated, and the organic layer was dried over magnesium sulfate, filtered, and concentrated to yield a residue. Heptanes was added, and the resulting mixture was concentrated to yield a residue.
Workup
- temperatureThe resulting viscous solution was cooled to 0° C.
- customThe layers were separated
- dry with materialthe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto yield a residue
- concentrationthe resulting mixture was concentrated
- customto yield a residue
Sources & evidence
- ORD record
- ord-93dda5b7462547b98c24097ff33c1247
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786116B2
Reaction notes
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