Lithium borohydride → HCID 18779759, compound

HRID 1421749Notes

Reaction equation

HRID 1421749 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=1.[Li+].[BH4-]>C1COCC1>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 54500758HCID 54500758, compound

Product 1

HCID 18779759HCID 18779759, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Cyano-3-(4-phenyl-butoxy)-benzoic acid methyl ester from step 1 (285.1 mg, 0.92 mmol) was dissolved in THF (4.6 ml). LiBH4 in THF (2 M, 923 μl, 1.85 mmol) was added. The reaction mixture was heated to 70° C. for 3 hours. The reaction mixture was quenched carefully with 3N HCl and then extracted with EtOAc (3×10 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield the desired product.

Workup

  1. customThe reaction mixture was quenched carefully with 3N HCl
  2. extractionextracted with EtOAc (3×10 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b81bfa936c6a46e9ba3e6ce936057630
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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