4-Cumylphenol → (+/-) cis-1-[4-(1-Methyl-1-phenylethyl)phenoxymethyl]-2-phthalimidocyclopentane

HRID 399044Notes

Reaction equation

HRID 399044 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]([C:47]1[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([CH3:40])[CH3:39].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:40][C:38]([C:41]1[CH:46]=[CH:45][C:44]([O:1][CH2:2][C@@H:3]2[CH2:7][CH2:6][CH2:5][C@@H:4]2[N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])=[CH:43][CH:42]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH3:39]

Participants

6

Reactant 4

HCID 117424-CumylphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54209124(+/-) cis-1-Hydroxymethyl-2-phthalimidocyclopentane

Product 1

HCID 67573820(+/-) cis-1-[4-(1-Methyl-1-phenylethyl)phenoxymethyl]-2-phthalimidocyclopentaneYield 26.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of (±) cis-1-hydroxymethyl-2-phthalimidocyclopentane (1.0 g, 4.08 mmol), triphenylphosphine (1.28 g, 4.9 mmol) and 4-cumylphenol (1.04 g, 4.9 mmol) in dry tetrahydrofuran (40 ml) was added diethyl azodicarboxylate (0.77 ml, 4.9 mmol). The mixture was allowed to warm to room temperature and stirred for 48 h. The reaction was poured into ice water (200 ml) and extracted into diethyl ether (3×100 ml). The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting crude product was purified by chromatography on a silica gel column eluting with 10-40% diethyl ether in petroleum ether 40-60. Pooling of pure fractions afforded the title compound as a colourless oil (0.48 g). Additional fractions afforded a further 0.76 g of product which was slightly contaminated with 4-cumylphenol.

Workup

  1. extractionextracted into diethyl ether (3×100 ml)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product was purified by chromatography on a silica gel column
  6. washeluting with 10-40% diethyl ether in petroleum ether 40-60

Sources & evidence

ORD record
ord-8d95a9c0217b4b68876d0495d75d8445
Source dataset
uspto-grants-1998_10
Patent number
US05817698

Reaction notes

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