Hydrochloric Acid → 4-(Thiophen-2-yl)butan-1-ol

HRID 978458Notes

Reaction equation

HRID 978458 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C:9](O)=[O:10].B.Cl>C1COCC1>[OH:10][CH2:9][CH2:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 783864-(2-Thienyl)Butyric Acid

Product 1

HCID 126238624-(Thiophen-2-yl)butan-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cool (0°) solution of 10.0 g of 4-thienylbutyric acid (58.8 mmol) in 60 ml of dry THF was added 59 ml of a 1M solution of borane in THF, dropwise with stirring over one hour. The mixture was stirred for an additional 5 hours. The reaction mixture was poured onto 200 g of ice. This mixture was acidified with 2N HCl and the product extracted into ethyl acetate. The extract was washed with brine, dried (Na2SO4) and evaporated to give 8.5 g of a colorless oil (93%). 1H-NMR (CDCl3)δ7.0 (1H, t); 6.75 (2H, m); 3.5 (2H, t); 2.75 (2H, t); 1.6 (4H, m).

Workup

  1. stirringThe mixture was stirred for an additional 5 hours
  2. extractionthe product extracted into ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-6083763d2cb6405ba7d07dbfe6c8c929
Source dataset
uspto-grants-1987_05
Patent number
US04665090

Reaction notes

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