Tributylphosphine → Ethyl {[2-methyl-4-({1-[4'-(trifluoromethyl)-4-biphenylyl]pentyl}oxy)phenyl]oxy}acetate

HRID 1391747Notes

Reaction equation

HRID 1391747 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.P(CCCC)(CCCC)CCCC.O[C:37]1[CH:49]=[CH:48][C:40]([O:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:39]([CH3:50])[CH:38]=1>C1COCC1>[CH3:50][C:39]1[CH:38]=[C:37]([O:20][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:22])[F:1])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:49]=[CH:48][C:40]=1[O:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 596742571-[4'-(Trifluoromethyl)-4-biphenylyl]-1-pentanol

Product 1

HCID 86604657Ethyl {[2-methyl-4-({1-[4'-(trifluoromethyl)-4-biphenylyl]pentyl}oxy)phenyl]oxy}acetateYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[4′-(trifluoromethyl)-4-biphenylyl]-1-pentanol (250 mg, 0.81 mmol) in dry THF (20 mL) under nitrogen at 0° C. (ice/water bath) was added nBu3P (0.41 mL, 1.64 mmol), followed by ethyl (4-hydroxy-2-methylphenoxy)acetate (170 mg, 0.81 mmol) and ADDM (420 mg, 1.64 mmol) portion-wise. After stirring the mixture for 18 hours at rt under nitrogen the solvent was removed under vacuum. The residue was partitioned between water and EtOAc and the aqueous re-extracted with EtOAc (3×30 mL). The organic combined extract was dried (MgSO4) and then reduced under vacuum. Purification by flash chromatography (silica), eluting with cyclohexane:EtOAc (9:1) afforded the title compound as a colourless gum (310 mg).

Workup

  1. customwas removed under vacuum
  2. customThe residue was partitioned between water and EtOAc
  3. extractionthe aqueous re-extracted with EtOAc (3×30 mL)
  4. extractionThe organic combined extract
  5. dry with materialwas dried (MgSO4)
  6. customPurification by flash chromatography (silica)
  7. washeluting with cyclohexane:EtOAc (9:1)

Sources & evidence

ORD record
ord-120236c456054dc093758b5e3d8d6422
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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