Sodium borohydride → HCID 20206262, compound

HRID 543343Notes

Reaction equation

HRID 543343 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:21])[CH2:19][CH3:20])=[CH:13][CH:12]=1)=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].CC(=CCC1C=CC(OC(C)CC)=CC=1)CC(OCC)=O.[BH4-].[Na+]>O.[Ni](Cl)Cl.CO>[CH3:1][CH:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:21])[CH2:19][CH3:20])=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 53748269HCID 53748269, compoundHCID 54423950HCID 54423950, compound

Product 1

HCID 20206262HCID 20206262, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalyst2×HCID 24385Nickel DichlorideCatalyst3×HCID 887MethanolSolvent2×

Procedure

A mixture (2.90 g, 10.0 mmol) of ethyl 3-methyl-5-[4-(1-methylpropoxy)phenyl]-2-pentenoate and ethyl 3-methyl-5-[4-(1-methylpropoxy)phenyl]-3-pentenoate is combined with nickel chloride (129 mg, 1.0 mmol) and 80 ml of methanol and heated to 50°. Water (10 drops) is added to dissolve the nickel chloride. A second portion of nickel chloride (129 mg, 1.0 mmol) is heated with 10 drops of water, and the resulting solution is added, with 2 ml of methanol, to the mixture. The mixture is chilled to 15°, and sodium borohydride (757 mg, 20.0 mmol) is added in portions over 10 min. The mixture is allowed to warm to RT, and after 3.5 hours the nickel is removed by filtration. The filtrate is washed with methanol and concentrated in vacuo and water and ether are added. The aqueous phase is extracted with ether and the combined organic phases are washed with brine, dried, filtered and the filtrate concentrated to give ethyl 3-methyl-5-[4-(1-methylpropoxy)phenyl]pentanoate.

Workup

  1. temperatureheated to 50°
  2. temperatureThe mixture is chilled to 15°
  3. customafter 3.5 hours the nickel is removed by filtration
  4. washThe filtrate is washed with methanol
  5. concentrationconcentrated in vacuo and water and ether
  6. additionare added
  7. extractionThe aqueous phase is extracted with ether
  8. washthe combined organic phases are washed with brine
  9. customdried
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-bed52246957341afb8f7779461c5cd5e
Source dataset
uspto-grants-1987_04
Patent number
US04661617

Reaction notes

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