Triethyl phosphite → Diethyl undec-10-en-1-ylphosphonate

HRID 985360Notes

Reaction equation

HRID 985360 reaction equation
C([O:3][P:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.I[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]>>[CH2:9]([O:8][P:4]([O:5][CH2:6][CH3:7])([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH2:12])=[O:3])[CH3:10]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 1111946211-Iodoundec-1-ene

Product 1

HCID 23420214Diethyl undec-10-en-1-ylphosphonate

Procedure

Triethylphosphite (12.2 mL, 71 mmol, 10 equiv) was added to 3 (2.0 g, 7.1 mmol, 1.0 equiv) and the mixture was stirred at reflux for 15 h. The excess triethylphosphite was removed by distillation and the remaining residue submitted to flash chromatography (SiO2, 5×15 cm, 25-50% ethyl acetate-hexanes gradient elution) to afford 4 (1.30 g, 2.1 g theoretical, 62%) as a colorless oil: 1H NMR (CDCl3, 250 MHz) δ 5.95-5.75 (m, 1H, RCH═CH2), 5.03-4.90 (m, 2H, RCH═CH2), 4.05 (m, 4H, CH3CH2OP), 2.02 (m, 2H, CH2CH═CH2), 1.80-1.20 (m, 20H); MALDI-FTMS (DHB) m/z 291.2088 (C15H31O3P+H+ requires 291.2089).

Workup

  1. temperatureat reflux for 15 h
  2. customThe excess triethylphosphite was removed by distillation
  3. washthe remaining residue submitted to flash chromatography (SiO2, 5×15 cm, 25-50% ethyl acetate-hexanes gradient elution)
  4. customto afford 4 (1.30 g, 2.1 g theoretical, 62%) as a colorless oil

Sources & evidence

ORD record
ord-879b78c048754cb1a5b064eed45b5c31
Source dataset
uspto-grants-2005_03
Patent number
US06872574B2

Reaction notes

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