Sodium Hydroxide → 3-Amino-1-(thiophen-3-yl)propan-1-ol
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]=[C:8]([C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)[CH2:9][C:10]#[N:11].[OH-].[Na+]>C1COCC1>[NH2:11][CH2:10][CH2:9][CH:8]([C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)[OH:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a stirred suspension of LAH (1.45 g, 38.1 mmol) in dry THF (120 mL) was added a solution of 3-oxo-3-(thiophen-3-yl)propanenitrile (4.8 g, 31.8 mmol) in dry THF (40 mL) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to 25° C. and then heated at 65° C. for 6 hours. After cooling to 0° C., a saturated solution of sodium hydroxide (2 mL) was added dropwise and the mixture was filtered. The filtrate was concentrated to dryness to give crude 3-amino-1-thiophen-3-yl-propan-1-ol which was used in next step without further purification. 1H NMR (300 MHz, CDCl3): δ 7.29-7.26 (m, 2H), 7.05 (dd, 1H, J1=4.8 Hz, J2=1.2 Hz), 5.04 (dd, 1H, J1=8.1 Hz, J2=3.0 Hz), 3.10-3.05 (m, 2H), 1.82-1.77 (m, 2H).
Workup
- temperatureheated at 65° C. for 6 hours
- temperatureAfter cooling to 0° C.
- filtrationthe mixture was filtered
- concentrationThe filtrate was concentrated to dryness
Sources & evidence
- ORD record
- ord-ad1bf0ec1b4040f3b4412f8df704356e
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673905B2
Reaction notes
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