Triphenylphosphine → HCID 86592641, compound

HRID 229315Notes

Reaction equation

HRID 229315 reaction equation
O[C:2]1[CH:7]=CN=C[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:41][O:42][CH:43]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58]CCC)[CH2:44][OH:45]>C1COCC1.N1C=CC=CC=1>[CH3:41][O:42][CH:43]([CH:46]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:3][CH2:2][CH3:7])[CH2:44][OH:45]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 53880301HCID 53880301, compoundHCID 178418642HCID 178418642, compound

Product 1

HCID 86592641HCID 86592641, compoundYield 199.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation of pyridine terminated 4-hexadecylethylene glycol monomethylether (Ligand 2). 4-hydroxypyridine (2.0 g, 22 mmol), triphenylphosphine (6.3 g, 24 mmol), and diisopropyl azodicarboxylate (4.8 g, 24 mmol) in THF (250 mL) were stirred at room temperature under nitrogen for 30 min.; hexadecylethylene glycol monomethylether (14.3 g, 20 mmol) was added, and the mixture was stirred overnight. THF was removed under vacuum, and the residue was purified by column chromatography eluting with chloroform:acetone:methanol mixtures to yield 2 (12.0 g, 78%). 1H NMR (300 MHz, CDCl3) δ 8.42 (d, aromatic), 6.82 (d, aromatic), 4.15 (t, pyr-O—CH2—CH2), 3.86 (t, pyr-O—CH2—CH2), 3.66 (br, CH2, 3.37 (s, CH3) ppm; 13C NMR (75 MHz, CDCl3) δ 164.7, 150.9, 110.2, 72.6, 71.8, 70.8, 70.4, 70.1, 67.1, 69.2, 58.9 ppm; HRMS calcd. 769.4441; Found M−H 768.4385.

Workup

  1. customterminated 4-hexadecylethylene glycol monomethylether (Ligand 2)
  2. customTHF was removed under vacuum
  3. customthe residue was purified by column chromatography
  4. washeluting with chloroform

Sources & evidence

ORD record
ord-54d89d869cab4250824d0a798c75061c
Source dataset
uspto-grants-2009_07
Patent number
US07563507B2

Reaction notes

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