Hydrochloric Acid → HCID 21412491, compound

HRID 2071837Notes

Reaction equation

C[P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.CO[C:15](=[O:23])[C:16]([CH3:22])([CH3:21])[CH2:17][CH2:18][CH2:19][CH3:20].Cl.[O:25]1[CH2:29]CCC1>CCOCC>[P:2]([O:25][CH2:29][C:15](=[O:23])[C:16]([CH3:21])([CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])([O:5][CH3:6])([O:3][CH3:4])=[O:7]

Participants

Conditions

Temperature: -78 °C

Procedure

Dimethyl methylphosphonate (14.88 g) is dissolved in dry tetrahydrofuran (THF, 34 ml) under a nitrogen atmosphere. The solution is cooled to -78° C. Butyllithium (7.68 g, 52 ml of 2.3 molar solution, 3 equiv.) is added very slowly during 1 hour. The mixture is stirred at -78° C for 15 minutes. A solution of 2,2-dimethylhexanoic acid methyl ester (6.32 g) in dry THF (16 ml) is added to the cold solution over a period of 1 hour. The mixture is stirred for 30 minutes and then allowed to warm up to room temperature. The reaction mixture is diluted with ether. Dilute (10%) hydrochloric acid (30 ml) is added and the reaction mixture shaken well. The organic phase is separated and washed several times with water, dried (MgSO4) and the solvent removed. The residue is distilled under reduced pressure to give the title compound, b.p. 110° - 120° C/0.1mm, γmaxfilm 1700, 1250, 1020 cm-1.

Workup

stirringThe mixture is stirred for 30 minutes
temperatureto warm up to room temperature
additionis added
stirringthe reaction mixture shaken well
customThe organic phase is separated
washwashed several times with water
dry with materialdried (MgSO4)
customthe solvent removed
distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record: ord-c44cf9a8d9244890b3e21d84c2903822
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04048328

Reaction notes

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