Methyl 5-phenylthiophene-3-carboxylate → (5-Phenylthiophen-3-yl)methanol

HRID 915693

Reaction equation

HRID 915693 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:7][CH:6]=1)=O>O1CCCC1>[C:10]1([C:8]2[S:7][CH:6]=[C:5]([CH2:3][OH:2])[CH:9]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 819151Methyl 5-phenylthiophene-3-carboxylate

Product 1

HCID 12941346(5-Phenylthiophen-3-yl)methanolYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Prepare a solution of 5-phenylthiophene-3-carboxylic acid methyl ester (500 mg, 2.29 mmol) in tetrahydrofuran (30 mL) and cool to 0° C. under nitrogen. Slowly add LiAl4 (1 M in tetrahydrofuran). After stirring for 1 hour at 0° C., quench the reaction with water, filter through Celite®, and rinse with ethyl acetate. Concentrate the filtrate to afford 416 mg of (5-phenylthiophene-3-yl)methanol as a white solid. 1H NMR (CDCl3) δ7.60-7.61 (m, 2H), 7.25-7.37 (m, 4H), 7.16 (s, 1H), 4.69 (d, J=2 Hz, 2H), 1.58 μm, 1H).

Workup

  1. customquench
  2. customthe reaction with water
  3. filtrationfilter through Celite®
  4. washrinse with ethyl acetate
  5. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-3b5122809e474dadacf3c203fa3e6058
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Linked notes

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