Cerium(III) chloride → HCID 54572386, compound

HRID 1731651Notes

Reaction equation

HRID 1731651 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:4]=[CH:3]1.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 14430179HCID 14430179, compound

Product 1

HCID 54572386HCID 54572386, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 0.36 g of methyl 4-oxocyclohex-2-enepropionate and 500 ml of 0.4M cerium chloride in methanol there was added carefully 0.07 g of sodium borohydride and the mixture was stirred for 10 minutes at room temperature. The reaction was quenched with 2 ml of water and the methanol solvent was removed under reduced pressure. The residue was partitioned between 10 ml of water and 50 ml of ether and the separated organic layer was dried over magnesium sulfate. Evaporation of the solvent from the organic solution gave methyl 4-hydroxycyclohex-2-enepropionate as a clear oil which was used without further purification. 1H NMR (CDCl3) δ 3.56 (s, 3H); 3.90-4.30 (m, 1H); 5.50-5.75 (m, 2H).

Workup

  1. customThe reaction was quenched with 2 ml of water
  2. customthe methanol solvent was removed under reduced pressure
  3. customThe residue was partitioned between 10 ml of water and 50 ml of ether
  4. dry with materialthe separated organic layer was dried over magnesium sulfate
  5. customEvaporation of the solvent from the organic solution

Sources & evidence

ORD record
ord-18b35497b407447c86fa0e9444abbf6c
Source dataset
uspto-grants-1986_11
Patent number
US04622422

Reaction notes

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