Thiophene → HCID 59207292, compound

To a stirred solution of thiophene (5.0 g, 59.5 mmol) in dry THF (50 ml) is added n-butyllithium (2.5 M in hexanes, 20.0 ml, 50.0 mmol) dropwise at −78° C. under nitrogen. After complete addition, the mixture is allowed to warm to room temperature, with stirring, over 2 h, followed by the addition of 1-chloro-6-iodohexane (12.3 g, 50.0 mmol). The resultant mixture is stirred overnight at room temperature. The reaction is quenched with sat. aq. ammonium chloride, and the reaction mixture is extracted with ethyl acetate (3×70 ml). The combined organic extracts are washed with water, brine, and dried over magnesium sulphate. The solvent is removed under reduced pressure and the residue is chromatographed (silica gel, petroleum ether), to give a pale yellow oil (9.3 g, 92%). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.06 (dd, J=5.1 Hz, 1.2 Hz, 1H, Ar—H), 6.87 (dd, J=5.1 Hz, 3.4 Hz, 1H, Ar—H), 6.75 (m, 1H, Ar—H), 3.48 (t, J=6.6 Hz, 2H, ClCH2), 2.80 (t, J=7.4 Hz 2H, ArCH2), 1.61-1.78 (m, 4H, CH2), 1.29-1.50 (m, 4H, CH2); 13C NMR (75 MHz, CDCl3): δ (ppm) 145.5 (quat.), 126.7 (CH), 124.1 (CH), 122.9 (CH), 45.1 (CH2), 32.6 (CH2), 31.7 (CH2), 29.9 (CH2), 28.4 (CH2) 26.7 (CH2); MS (m/e) 204 (M+, 9%), 202 (M+, 3%), 97 (100).

1. additionAfter complete addition
2. customThe reaction is quenched with sat. aq. ammonium chloride
3. extractionthe reaction mixture is extracted with ethyl acetate (3×70 ml)
4. washThe combined organic extracts are washed with water, brine
5. dry with materialdried over magnesium sulphate
6. customThe solvent is removed under reduced pressure
7. customthe residue is chromatographed (silica gel, petroleum ether)

ORD record

ord-6c4a6fb802be49a0b79c4459f28c7d95

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674397B2