Ammonium Chloride → 1-(2-Thienyl)benzyl alcohol

HRID 1899713Notes

Reaction equation

HRID 1899713 reaction equation
[BH4-].[Na+].[CH2:3]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6]C=1.[Cl-].[NH4+].CO.C1C[O:22][CH2:21]C1>>[S:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[C:3]1([CH:4]=[CH:9][CH:8]=[CH:7][CH2:6]1)[CH2:21][OH:22]

Participants

5

Reactant 4

HCID 25517Ammonium ChlorideHCID 139391Thiophene, 2-(phenylmethyl)-HCID 4311764Sodium borohydrideHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 699479851-(2-Thienyl)benzyl alcoholYield 92%

Procedure

Sodium borohydride (0.37 g, 10 mmol) was added to 2-benzylthiophene (1.88 g, 10 mmol) dissolved in methanol/THF mixture (1:10 ratio, 11 ml). This was stirred at room temperature for 10 h. The reaction mixture was decomposed by addition of saturated ammonium chloride solution (50 ml) and was extracted with ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous MgSO4. Removal of the solvent gave 1-(2-thienyl)benzyl alcohol as a solid (1.75 g, 92% yield).

Workup

  1. extractionwas extracted with ethyl acetate (2×50 ml)
  2. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-20471e16f5c446b88a39a30041c66474
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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