Methanol → HCID 18347204, compound

HRID 441167Notes

Reaction equation

HRID 441167 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[C:9]=1[CH2:10][C:11]#[N:12])=O.[Li+].[BH4-].CO.[NH4+].[Cl-]>C1COCC1.CC(C)=O>[OH:2][CH2:3][C:5]1[S:6][C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[C:9]=1[CH2:10][C:11]#[N:12]

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 54307398HCID 54307398, compound

Product 1

HCID 18347204HCID 18347204, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-cyanomethyl-4-(4-(methylthio)phenyl)-5-phenylthiophene-2-carboxylic acid methyl ester (480 mg) (Step 1) in THF (13 mL) was added 55 mg of LiBH4 followed by 50 μL of MeOH; then the mixture was heated at 50° C. for 90 min. After cooling to r.t. a few drops of acetone were slowly added, then a saturated solution of NH4Cl. The mixture was then extracted twice with EtOAc, the organic layers combined, washed with brine, dried over MgSO4, filtered and the solvent evaporated under vacuum. Purification by silica gel chromatography using 30% of EtOAc in hexane afforded the title compound.

Workup

  1. additionwere slowly added
  2. extractionThe mixture was then extracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-1979d52ebf064051a7ec12a974a9d5bb
Source dataset
uspto-grants-1996_05
Patent number
US05521213

Reaction notes

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