Triethyl Phosphate → [5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-ynyl]-phosphonic acid diethyl ester

HRID 1514337Notes

Reaction equation

HRID 1514337 reaction equation
Br[CH2:2][CH2:3][C:4]#[C:5][CH2:6][O:7][Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[P:25](OCC)([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26]>>[CH2:28]([O:27][P:25]([CH2:2][CH2:3][C:4]#[C:5][CH2:6][O:7][Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:26])[O:30][CH2:31][CH3:32])[CH3:29]

Participants

3

Reactant 2

HCID 6535Triethyl PhosphateHCID 57829248(5-Bromo-pent-2-ynyloxy)-tert-butyl-diphenyl-silane

Product 1

HCID 57829237[5-(tert-Butyl-diphenyl-silanyloxy)-pent-3-ynyl]-phosphonic acid diethyl esterYield 98%

Procedure

A mixture of compound 6 (3.24 g, 80.7 mmol) and triethyl phosphate (40 mL) was refluxed under nitrogen atmosphere for overnight. After evaporation, the residue was purified with 50% EtOAc in hexanes by silica gel column chromatography to give 3.26 g of product 7 (7.90 mmol, 98% yield); 1H NMR (CDCl3) δ 7.77˜7.64 (m, 4H), 7.46˜7.32 (m, 6H), 4.29 (t, J=1.9 Hz, 2H), 4.16˜4.02 (m, 4H), 2.50˜2.34 (m, 2H), 1.96˜1.82 (m, 2H), 1.31 (t, J=7.1 Hz, 6H), 1.04 (s, 9H); 31P NMR (CDCl3) δ 30.43.

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for overnight
  2. customAfter evaporation
  3. customthe residue was purified with 50% EtOAc in hexanes by silica gel column chromatography

Sources & evidence

ORD record
ord-b7915f83b1244218abfce800362c7e9c
Source dataset
uspto-grants-2012_07
Patent number
US08222257B2

Reaction notes

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