Hydrochloric Acid → HCID 18325913, compound

HRID 1251028Notes

Reaction equation

HRID 1251028 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3]1.[BH4-].[Na+].Cl>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10922777HCID 10922777, compound

Product 1

HCID 18325913HCID 18325913, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 4-oxo-2-phenylcyclohex-2-enecarboxylate(500 mg, 2.05 mmol) in MeOH(10 ml) at 0° C., NaBH4(77.5 mg, 2.05 mmol) was added by portions. After stirring for 45 minutes, dil.HCl aq. was added to the reaction mixture and the solvent was evaporated under reduced pressure. The residue was added water and extracted with AcOEt. The organic layer was washed with water and brine, dried over MgSO4. Concentration of the organic layer afford 504 mg of ethyl 4-hydroxy-2-phenylcyclohex-2-enecarboxylate(y=100%) as a pale yellow crystal. 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.23-7.34(5H, m), 6.10-6.22(1H, m), 4.30-4.50(1H, m), 3.90-4.08(1H, m), 3.72 and 3.64(1H, t and t, J=5.8 and 5.3 Hz), 1.60-2.30(4H, m), 1.00 and 1.10(3H, m).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe residue was added water
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-cdcd343d48f1423fb29b6be66f8f5cf0
Source dataset
uspto-grants-2002_01
Patent number
US06340772B1

Reaction notes

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