3-Cyclopentene-1-carboxylic acid → 2-Phenylpropan-2-yl cyclopent-3-enecarboxylate

HRID 42550Notes

Reaction equation

HRID 42550 reaction equation
ClC(Cl)(Cl)C(=N)O[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[CH:17]1([C:22]([OH:24])=[O:23])[CH2:21][CH:20]=[CH:19][CH2:18]1>C1CCCCC1.C(Cl)Cl>[CH:17]1([C:22]([O:24][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:7])[CH3:6])=[O:23])[CH2:21][CH:20]=[CH:19][CH2:18]1

Participants

5

Reactant 2

HCID 8537563-Cyclopentene-1-carboxylic acidHCID 111405172-Phenylpropan-2-yl 2,2,2-trichloroacetimidate

Product 1

HCID 594750152-Phenylpropan-2-yl cyclopent-3-enecarboxylateYield 90.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

A solution of 2-phenylpropan-2-yl 2,2,2-trichloroacetimidate (23.85 g, 85 mmol) in cyclohexane (85 mL) was treated with a solution of cyclopent-3-enecarboxylic acid (4.77 g, 42.5 mmol) in methylene chloride (43 mL), and the mixture was stirred for about 16 hours at room temperature during which time a colorless solid precipitated. The precipitate was collected by filtration and rinsed with hexanes. The combined filtrates were concentrated in vacuo to yield a residue. The residue was purified over a 330 g silica gel column, eluting at 100 mL/min with a 0-5% ethyl acetate/hexanes gradient over 2 column volumes, then 5% ethyl acetate/hexanes for 2 column volumes, then a 5-40% ethyl acetate/hexanes gradient over 10 column volumes to yield 2-phenylpropan-2-yl cyclopent-3-enecarboxylate (8.84 g, 38.4 mmol, 90% yield) as a yellow oil.

Workup

  1. customprecipitated
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with hexanes
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. customto yield a residue
  6. customThe residue was purified over a 330 g silica gel column
  7. washeluting at 100 mL/min with a 0-5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-47c072a85a934729b05d7cc02cece912
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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