Hydrochloric Acid → Dimethyl [2-oxo-3-(indol-5yloxy)propyl]phosphonate

HRID 1579495Notes

Reaction equation

C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][C:24](OCC)=[O:25])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.Cl>CCCCCC.O1CCCC1>[O:25]=[C:24]([CH2:23][O:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[NH:13][CH:14]=[CH:15]2)[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyl-lithium (21.8ml. of a 2.92M solution in hexane) was added to a solution of dimethyl methylphosphonate (6.2g.) in dry tetrahydrofuran (50ml.) at -78°C. in an atmosphere of argon. After 10 minutes, a solution of ethyl 5-indolyloxyacetate (5.5g.) in dry tetrahydrofuran (50ml.) was added dropwise, and the mixture was stirred for 2 hours at -78°C. The reaction mixture was poured into 2N hydrochloric acid and stirred vigorously for 5 minutes, then the solvents were evaporated under reduced pressure. The residue was shaken with a mixture of ethyl acetate and water, and the organic phase was separated and washed with brine. The solution was dried, the solvents were evaporated and the residue was chromatographed on a column of silica gel MFC (250 g.)using methylene dichloride : ethyl acetate mixtures as eluant, to give dimethyl [2-oxo-3-(indol-5yloxy)propyl]phosphonate as an oil, RF = 0.3 (ethyl acetate).

Workup

stirringstirred vigorously for 5 minutes
customthe solvents were evaporated under reduced pressure
stirringThe residue was shaken with a mixture of ethyl acetate and water
customthe organic phase was separated
washwashed with brine
customThe solution was dried
customthe solvents were evaporated
customthe residue was chromatographed on a column of silica gel MFC (250 g

Sources & evidence

ORD record: ord-d288cf5d38214781a610c26636e06b95
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03931206

Reaction notes

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