Sodium borohydride → HCID 14986699, compound

HRID 1494140Notes

Reaction equation

HRID 1494140 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=1)[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10].[BH4-].[Na+]>[Co](Cl)Cl.CO>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54096745HCID 54096745, compound

Product 1

HCID 14986699HCID 14986699, compound

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 0.422 g (1.2 mmol) methyl 8-chloro-4[m-(3-pyridyl)phenyl]oct-2-enoate, 0.097 g (0.41 mmol) cobalt (II) chloride and 8 mL methanol at 0° C. is added slowly 0.105 g (2.8 mmol) of sodium borohydride. The resulting black suspension is stirred at 0° C. for 30 minutes and then filtered through activated magnesium silicate (Florisil) and the filter cake is washed several times with methanol. The solvent is evaporated to obtain methyl 8-chloro-4-[m-(3-pyridyl)-phenyl]octanoate; IR (CH2Cl2): 1732 cm-1.

Workup

  1. filtrationfiltered through activated magnesium silicate (Florisil)
  2. washthe filter cake is washed several times with methanol
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-8c527c438d244739a79d7d6d078fe8a9
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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