Triphenylphosphine → Methyl 3-[[3-(cyclopentyloxy)-4-methoxyphenyl]methoxy]benzoate

HRID 2395398Notes

Reaction equation

HRID 2395398 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH:15]1([O:20][C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH2:24][OH:25])[CH2:19][CH2:18][CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:50][O:51][C:52](=[O:60])[C:53]1[CH:58]=[CH:57][CH:56]=[C:55](O)[CH:54]=1>O1CCCC1>[CH:15]1([O:20][C:21]2[CH:22]=[C:23]([CH2:24][O:25][C:55]3[CH:54]=[C:53]([CH:58]=[CH:57][CH:56]=3)[C:52]([O:51][CH3:50])=[O:60])[CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 5363146Diisopropyl azodicarboxylateHCID 111387063-Cyclopentyloxy-4-methoxybenzyl alcohol

Product 1

HCID 18971820Methyl 3-[[3-(cyclopentyloxy)-4-methoxyphenyl]methoxy]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (1.2 ml, 5.99 mmol, 1.2 eq)was added to a mixture of (1.10 g,4.99 mmol, 1.0 eq) 3-cyclopentyloxy-4-methoxybenzyl alcohol, (1.44 g, 5.49 mmol, 1.1 eq) triphenylphosphine, and (0.75 g, 4.99 mmol, 1.0 eq) methyl-3-hydroxy-benzoate in 30 ml of anhydrous tetrahydrofuran. After stirring for 18 hours at room temperature the reaction mixture was concentrated in vacuo and chromatographed on a silica gel column, eluting with 10%, then 15% ethyl acetate-hexane to yield 897 mg, 50%, of a clear oil. High Resolution Mass Spectra: Calc'd 356.1624. Found: 356.1600.

Workup

  1. concentrationwas concentrated in vacuo
  2. customchromatographed on a silica gel column
  3. washeluting with 10%
  4. custom15% ethyl acetate-hexane to yield 897 mg, 50%

Sources & evidence

ORD record
ord-03b7c73e98bb414e86bf791525365dab
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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