Triethyl phosphite → Triethyl phosphite

HRID 1982187Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:10])[CH:4](Br)[CH2:5][CH:6]([CH3:8])[CH3:7].[P:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>>[P:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].[CH3:1][O:2][C:3](=[O:10])[CH:4]([P:11]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:18])[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 12957039Methyl 2-bromo-4-methylpentanoate

Product 2

HCID 31215Triethyl phosphite

HCID 13653348HCID 13653348, compound

Conditions

Temperature: 200 °C

Procedure

2-Bromo-4-methyl-pentanoic acid methyl ester (193 g, 0.92M) and triethyl phosphite (330 ml, 1.84M) were heated to 150°. The reaction temperature was increased to 200° C. over 6 h and a distillate b.p. 37°-60° C. (80 g) collected with an air condenser. The residue was distilled under high vacuum to afford 2 fractions (a) mainly triethyl phosphite b.p. 40°-80° C. at 0.4 mm Hg and (b) 4-methyl-2-(diethyl phosphono)pentanoic acid methyl ester (188 g) b.p. 96°-100° C. at 0.4 mm Hg (Found: C, 47.6; H, 8.6.C11H23O5P+0.6H2O requires C, 47.7; H, 8.8%); δ(CDCl3) 0.9 (6H, dd, J=7 Hz, J=7 Hz, (CH3)2C); 1.04-2.10 (3H, m, CH2CH); 1.34 (6H, t, J=7 Hz, (CH2CH3)2); 3.09 (1H, ddd, J=23 Hz, J=10 Hz, J=4 Hz, CHP); 3.73 (3H, s, CH3O); 4.14 (4H, m, (CH2CH3)2).

Workup

distillationa distillate b.p. 37°-60° C. (80 g) collected with an air condenser
distillationThe residue was distilled under high vacuum

Sources & evidence

ORD record: ord-de47d013218e4e989480f74abb363061
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04595700

Reaction notes

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