Triethyl phosphite → HCID 54362658, compound

HRID 458067Notes

Reaction equation

HRID 458067 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([CH2:11]Br)[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2].[P:14]([O:21]CC)([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]>>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([CH2:11][P:14]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:21])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 22970375Ethyl 3-(bromomethyl)-5-methylhexanoate

Product 1

HCID 54362658HCID 54362658, compoundYield 48%

Conditions

Temperature
190 °C

Procedure

3-Bromomethyl-3-isobutyl-propionic acid ethyl ester (4.6 g, 18.3 mmol) is warmed in a 170° C. oil bath under Ar. Triethyl phosphite (3.6 g, 22 mmol) is added dropwise over 2 hours. When addition is complete, the oil bath temperature is raised to 190° C. for 4 hours. The reaction mixture is cooled to room temperature, and the product is purified by MPLC in EtOAc to give 2.7 g (48% yield) of 3-(diethoxy-phosphorylmethyl)-5-methyl-hexanoic acid ethyl ester. NMR (H1, 400 MHz, CDCl3) δ 0.8 (6H, d); δ 1.2 (5H, m); δ 1.3 (6H, m); δ 1.6 (1H, m); δ 1.7 (1H, d); δ 1.8 (1H, d); δ 2.3 (2H, m); δ 2.5 (1H, dd); δ 4.1 (6H, m).

Workup

  1. additionWhen addition
  2. temperatureThe reaction mixture is cooled to room temperature
  3. customthe product is purified by MPLC in EtOAc

Sources & evidence

ORD record
ord-db1df7df7f06432aa4c937788ded2d4b
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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