Benzoin → HCID 10927656, compound

HRID 377319Notes

Reaction equation

HRID 377319 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][C@H:7]1[C:11]([C:12]([OH:14])=O)=[CH:10][CH2:9][CH2:8]1.S(Cl)(Cl)=O.[C:22]1([C:28]([CH:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)O)=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])(=O)C.[NH4+:42]>CN(C)C=O.C(O)(=O)C.N1C=CC=CC=1.C(Cl)Cl>[C:22]1([C:28]2[N:42]=[C:12]([C:11]3[C@H:7]([CH2:6][C:5]4[CH:15]=[CH:16][CH:17]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:8][CH2:9][CH:10]=3)[O:14][C:30]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

9

Reactant 4

HCID 8400BenzoinHCID 24386Thionyl ChlorideHCID 517165Ammonium AcetateHCID 54280380HCID 54280380, compound

Product 1

HCID 10927656HCID 10927656, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 176Acetic AcidSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A methylene chloride solution (20 ml) of (-)-5(S)-(3-methoxybenzyl)-1-cyclopentenecarboxylic acid (1.99 g), thionyl chloride (2 ml) and N,N-dimethylformamide (2 drops) was stirred for 3 hours at room temperature. Removal of solvent at reduced pressure afforded the crude acid chloride as a brown oil. To a methylene chloride solution (20 ml) of the crude acid chloride and benzoin (1.97 g), pyridine (2 ml) was added at room temperature. The solution was stirred for 4 hours at the same temperature and washed with IN hydrochloric acid (×2) and brine. Drying (sodium sulfate) and removal of solvent afforded a yellow oil. An acetic acid solution (80 ml) of the yellow oil and ammonium acetate (14.98 g) was stirred for 7.5 hours at 130° C. and cooled to room temperature. Solvent was removed and the residue was dissolved in ethyl acetate. The solution was washed with water, saturated aqueous sodium hydrogen carbonate (×3), water, and brine. Drying (sodium sulfate) and removal of solvent at reduced pressure followed by flash chromatography on 100 g of silica afforded (+)-1-(4,5-diphenyloxazol-2-yl)-5(S)-(3-methoxybenzyl)cyclopentene as a pale yellow solid (2.69 g, 99.6% ee).

Workup

  1. customRemoval of solvent at reduced pressure
  2. customafforded the crude acid chloride as a brown oil
  3. washwashed with IN hydrochloric acid (×2) and brine
  4. customDrying
  5. custom(sodium sulfate) and removal of solvent
  6. customafforded a yellow oil
  7. customSolvent was removed
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washThe solution was washed with water, saturated aqueous sodium hydrogen carbonate (×3), water, and brine
  10. customDrying
  11. custom(sodium sulfate) and removal of solvent at reduced pressure

Sources & evidence

ORD record
ord-567ea8fe442044b584120d5cfee64cb0
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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