Sodium hydride → Dimethyl (1-bromo-2-oxooctyl)phosphonate

HRID 441571Notes

Reaction equation

HRID 441571 reaction equation
[H-].[Na+].[CH3:3][O:4][P:5]([CH2:9][C:10](=[O:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:8])[O:6][CH3:7].[H][H].[Br:20]N1CCCCCC1=O>C1C=CC=CC=1>[CH3:3][O:4][P:5]([CH:9]([Br:20])[C:10](=[O:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:8])[O:6][CH3:7]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 755411-Bromoazepan-2-oneHCID 13390134Dimethyl (2-oxooctyl)phosphonateHCID 178418361HCID 178418361, compound

Product 1

HCID 54443054Dimethyl (1-bromo-2-oxooctyl)phosphonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a benzene suspension of 194 mg of 80% NaH in mineral oil, a solution of 1.62 g of dimethyl-(2-oxo-octyl)phosphonate in 5 ml of benzene was added dropwise and continually stirred until there was no more evolution of hydrogen. The 1.24 g of N-bromo-caprolactam were added to form the carbanion of dimethyl-(1-bromo-2-oxo-octyl)-phosphonate. After 15 minutes the solution of the aldehyde, prepared as described above, was added and the reaction mixture stirred for 15 minutes.

Sources & evidence

ORD record
ord-6ec53951e21e4c229980c0447bc29a5b
Source dataset
uspto-grants-1977_08
Patent number
US04041064

Reaction notes

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