Tetrahydrofuran → HCID 12828022, compound
Reaction equation
[H-].[Na+].[P:3]([O-:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].C12(C)C(C)(C)C(CC1)C[CH2+]2[CH2:20][CH2:21][CH2:22][C:23](=[O:25])[CH3:24].[O:27]1CC[CH2:29][CH2:28]1>>[CH2:28]1[CH2:29][O:25][C:23]([CH3:24])([CH2:22][CH2:21][CH2:20][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6])[O:27]1Participants
Procedure
To a solution of 5.5 g. of pure sodium hydride in 200 ml. of dry tetrahydrofuran under nitrogen, there is added one equivalent of dry diethyl phosphite. The mixture is cooled in an ice-bath and stirred at 0° for 1.5 hours. One equivalent of the ethylene ketal of 1-bormopentan-4-one in 60 ml. of dry tetrahydrofuran is added and the mixture stirred for 15 minutes at 0° and allowed to stand 16 hours at room temperature. The mixture is then heated under reflux for three hours, cooled and filtered. The filtrate is concentrated under reduced pressure and the concentrate taken up in ether. This mixture is shaken with saturated aqueous sodium chloride and then separated. The organic layer is separated and concentrated under reduced pressure to give diethyl 4,4-ethylenedioxypentylphosphonate (V) (R is ethyl) which is purified by distillation in vacuo (b.p. 115° at 0.05 mm.).
Workup
- temperatureThe mixture is cooled in an ice-bath
- stirringthe mixture stirred for 15 minutes at 0°
- waitto stand 16 hours at room temperature
- temperatureThe mixture is then heated
- temperatureunder reflux for three hours
- temperaturecooled
- filtrationfiltered
- concentrationThe filtrate is concentrated under reduced pressure
- stirringThis mixture is shaken with saturated aqueous sodium chloride
- customseparated
- customThe organic layer is separated
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e35dc5d3dd20476093197020c98ebce0
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03979458
Reaction notes
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