Tributylphosphine → 4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile

HRID 411537Notes

Reaction equation

HRID 411537 reaction equation
[OH:1][CH:2]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[CH2:3][CH:4]=[CH2:5].[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][C:21]1[CH:26]=[CH:25][C:24]([O:1][CH:2]([C:6]2[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=2)[CH2:3][CH:4]=[CH2:5])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 110193454-(1-Hydroxy-3-butenyl)benzonitrileHCID 117455194-[(Oxan-2-yl)oxy]phenol

Product 1

HCID 222356714-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrileYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) mixture of 4-(1-hydroxy-3-butenyl)benzonitrile (4.93 g, 28.5 mmol) and 4-(tetrahydro-2H-pyran-2-yloxy)phenol (8.3 g, 42.7 mmol) in dry THF (200 mL) was treated with tributylphosphine (8.85 mL, 42.7 mmol), followed by 1,1′-(azodicarbonyl)dipiperidine (10.77 g, 42.7 mmol). After addition was complete, the reaction mixture was stirred at 0° C. for 10 min, before being stirred at rt overnight. The precipitate of tributylphosphine oxide was removed by filtration and the filtrate was concentrated in vacuo to give 24.6 g of crude product. This was purified by chromatography on silica gel, eluting with IPA:EtOAc:heptane (5:5:90), to give 4.6 g (47%) of the subtitle compound.

Workup

  1. temperatureA cooled
  2. additionAfter addition
  3. stirringbefore being stirred at rt overnight
  4. customThe precipitate of tributylphosphine oxide was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give 24.6 g of crude product
  7. customThis was purified by chromatography on silica gel
  8. washeluting with IPA:EtOAc:heptane (5:5:90)

Sources & evidence

ORD record
ord-65dfd60b316c42f89cf75314fc85609f
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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