Ammonium Chloride → HCID 69609125, compound

HRID 1827292Notes

Reaction equation

HRID 1827292 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([CH3:17])C(OC)=O.[Cl-].[Li+].[BH4-].[Na+].[NH4+].[Cl-].C[CH2:25][OH:26].C1COCC1>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:17][CH2:25][OH:26]

Participants

6

Reactant 5

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 22136239HCID 22136239, compound

Product 1

HCID 69609125HCID 69609125, compound

Procedure

To a cold (0° C.) solution of methyl 2-(2-thienyl)phenylpropionate (387 mg, 1.57 mmol) and anhydrous lithium chloride (353 mg, 8.32 mmol) in an EtOH/THF mixture (4:3; 28 mL) was added sodium borohydride (315 mg, 8.32 mmol). The reaction mixture was then stirred at room temperature for 20 h. Aqueous NH4Cl (50 mL) was added and the crude product was extracted with EtOAc (2×50 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by flash chromatography (5% EtOAc in hexane) to yield 2-(2-thienyl)phenpropyl alcohol as a light yelllow oil.

Workup

  1. extractionthe crude product was extracted with EtOAc (2×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-666a5fdc272149bf891396799235778f
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

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