Methanol → 3-(Thiophen-2-yl)propan-1-ol

HRID 1511891Notes

Reaction equation

HRID 1511891 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8](O)=[O:9].CO.CCOCC.C(OCC)(=O)C>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 7031693-(2-Thienyl)propanoic acid

Product 1

HCID 131098663-(Thiophen-2-yl)propan-1-olYield 901.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane tetrahydrofuran complex (13.03 ml, 13.03 mmol) was added to THF (29.6 ml). 3-(thiophen-2-yl)propanoic acid (0.100 g, 0.640 mmol) was dissolved in THF (5 mL) and added slowly to the reaction. The solution was stirred overnight. Methanol was added and then the solution was rotovapped. More methanol was added and the solution was rotovapped. This was repeated once. The solution was passed through a pad of silica gel eluting with ether and then ethyl acetate and then rotovapped to give 3-(thiophen-2-yl)propan-1-ol (0.820 g, 5.77 mmol, 97% yield) as a light yellow oil: 1H NMR (400 MHz, CDCl3). δ ppm 7.12 (m, 1H), 6.92 (dd, 1H), 6.81 (m, 1H), 3.71 (t, 1H), 2.95 (t, 1H), 2.02-1.87 (m, 1H)

Workup

  1. additionadded slowly to the reaction

Sources & evidence

ORD record
ord-3093c0a4a3e0423f9bcdb89fe65fd70a
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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