Methanol → HCID 13423053, compound

HRID 1596475Notes

Reaction equation

HRID 1596475 reaction equation
[Li+].[BH4-].C[O:4][C:5](=O)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1.CO>C(OCC)C>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])=[CH:11][CH:12]=1)#[N:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 43378017HCID 43378017, compound

Product 1

HCID 13423053HCID 13423053, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiBH4 (1.5 g; 71.1 mmol) was added to a stirred solution of 4-(4-cyanophenoxy)butyric acid methyl ester (9.63 g; 47.4 mmol; from step (b) above), MeOH (2.87 mL; 71.1 mmol) and diethyl ether (158 mL) and the reaction mixture was refluxed overnight. The ether phase was collected and the residue was extracted with diethyl ether (3×50 mL). The combined organic phase was dried, concentrated and purified using column chromatography (EtOAc:hexane; 1:3) to give the sub-title compound (3.82 g; 21.8 mmol).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe ether phase was collected
  3. extractionthe residue was extracted with diethyl ether (3×50 mL)
  4. customThe combined organic phase was dried
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-931f8575d5b24010ba4f0d89f32a581f
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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