Triethyl phosphite → ethyl 4-diethoxyphosphoryl-3-oxobutanoate

HRID 2226658Notes

Reaction equation

[CH2:1]([O:3][P:4](C#CC1N(C2C=CC(F)=CC=2)C2C(C=1C(C)C)=CC=CC=2)([CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2].P(OCC)(OCC)[O:37][CH2:38][CH3:39]>>[CH2:38]([O:37][P:4]([O:3][CH2:1][CH3:2])([CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:39]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 131718372HCID 131718372, compound

Product 1

HCID 11129233ethyl 4-diethoxyphosphoryl-3-oxobutanoateYield 67%

Conditions

Temperature: 115 °C

Procedure

The title A compound of Example 3 (41.0 g, 0.174 mol) was dissolved in (EtO)3P (150 mL, 0.87 mol) and heated at 115° C. (bath temperature) for 18 hours and then cooled to room temperature. The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature). The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9), to give the title compound as a pale yellow liquid (31 g, 67%).

Workup

temperaturecooled to room temperature
distillationThe excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature)
customThe resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9)

Sources & evidence

ORD record: ord-42d32989fb6d4d01a642cb3c9f9ecb08
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05349069

Reaction notes

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