Triphenylphosphine → HCID 58629854, compound

HRID 1391742Notes

Reaction equation

HRID 1391742 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:6][CH:7]=1.O[C:15]1[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH3:28])[CH:16]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([O:13][C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH3:28])[CH:16]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 10847790HCID 10847790, compoundHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetate

Product 1

HCID 58629854HCID 58629854, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-bromophenyl)-1-pentanol (1.00 g, 4.11 mmol) in dry THF (40 mL) at 0° C. was added ethyl (4-hydroxy-2-methylphenoxy)acetate (865 mg, 4.11 mmol), PPh3 (1.30 g, 4.94 mmol) and ADDP (1.25 g, 4.94 mmol) and the reaction stirred for 30 minutes and then allowed to warm to rt overnight. The mixture was then reduced under vacuum and the residue partitioned between EtOAc and water and the layers separated. The organic layer was washed with water (2×) then brine, dried (Na2SO4) and reduced under vacuum to give a brown oil. Purification by Biotage™ chromatography (silica, 90 g cartridge) eluting with petroleum ether 40-60° C.:EtOAc (gradient 1:0 to 9:1) afforded the title compound as colourless oil (1.15 g).

Workup

  1. customthe residue partitioned between EtOAc and water
  2. customthe layers separated
  3. washThe organic layer was washed with water (2×)
  4. dry with materialbrine, dried (Na2SO4)
  5. customto give a brown oil
  6. customPurification by Biotage™ chromatography (silica, 90 g cartridge)
  7. washeluting with petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-50bfae4808ab414bb2e635c4d150276e
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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