Triethyl phosphite → HCID 86745095, compound

HRID 728882Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:12][CH:13]=[O:14])/[CH:5]=[C:6](/[CH2:10]Br)\[CH2:7][CH:8]=[CH2:9].[P:16]([O:23]CC)([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]>>[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:12][CH:13]=[O:14])/[CH:5]=[C:6](/[CH2:10][P:16]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:23])\[CH2:7][CH:8]=[CH2:9]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 21612924HCID 21612924, compound

Product 1

HCID 86745095HCID 86745095, compound

Procedure

3.7 g of E-2-formylamino-4-bromomethyl-3,6-heptadienoic acid methyl ester are dissolved in 37 ml of triethyl phosphite, and the mixture is heated at75° for 8 hours. Excess triethyl phosphite is then distilled off under a high vacuum. Purification by column chromatography (silica gel, methanol/ethyl acetate 1:10) yields E-2-formylamino-4-diethylphosphonomethyl-3,6-heptadienoic acid methyl ester in the form of a colourless oil, 1H-NMR (CDCl3): 2.54 (d,2H, P--CH2); 3.10 (m, 2H, C(5)--H); 5.10 (m, 2H, C(7)--H); 5.37 (d, 1 H, C(2)--H); 5.74 (m, 1 H, C(6)--H).

Workup

temperaturethe mixture is heated at75° for 8 hours
distillationExcess triethyl phosphite is then distilled off under a high vacuum
customPurification by column chromatography (silica gel, methanol/ethyl acetate 1:10)

Sources & evidence

ORD record: ord-b57b07c27a994eafa5de8c7e5a8118a1
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051413

Reaction notes

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