Benzoin → HCID 19358454, compound

HRID 377320Notes

Reaction equation

HRID 377320 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[CH:14][C:15]([OH:17])=O)[CH:6]=[CH:7][CH:8]=1.[C:18]1([C:24]([CH:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)O)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([N:36]=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:18]1([C:24]2[N:36]=[C:15]([CH2:14][C:10]3[CH2:11][CH2:12][CH2:13][C:9]=3[C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[O:17][C:26]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8400BenzoinHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 54130125HCID 54130125, compound

Product 1

HCID 19358454HCID 19358454, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(3-methoxyphenyl)-cyclopentylidene]acetic acid (4.0 g) in methylene chloride (80 ml) were added benzoin (3.7 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodimide (4.1 ml) and 4-dimethylaminopyridine (2.1 g). The resulting mixture was stirred at room temperature for 12 hours and then partitioned between ethyl acetate and 1N-hydrochloric acid. The organic layer was separated, washed successively with 1N-hydrochloric acid, saturated sodium bicarbonate aqueous solution, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue and ammonium acetate (6.6 g) were dissolved in acetic acid (40 ml) and refluxed for 4 hours. The reaction mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed by silica gel to give 2-[(4,5-diphenyloxazol-2-yl)methyl]-1-(3-methoxyphenyl)cyclopentene (4.1 g).

Workup

  1. custompartitioned between ethyl acetate and 1N-hydrochloric acid
  2. customThe organic layer was separated
  3. washwashed successively with 1N-hydrochloric acid, saturated sodium bicarbonate aqueous solution, and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue and ammonium acetate (6.6 g) were dissolved in acetic acid (40 ml)
  7. temperaturerefluxed for 4 hours
  8. customThe reaction mixture was evaporated in vacuo
  9. customthe residue was partitioned between ethyl acetate and water
  10. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated in vacuo
  13. customThe residue was chromatographed by silica gel

Sources & evidence

ORD record
ord-96d7e03fce5a4f58bd1aab88439f4281
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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