Thionyl Chloride → 4,5,6,7-Tetrahydro-1-benzothiophen-7-one

HRID 402128

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:2]1.S(Cl)(Cl)=O>COCCOCCOC.N1C=CC=CC=1>[S:1]1[C:2]2[C:9](=[O:11])[CH2:8][CH2:7][CH2:6][C:3]=2[CH:4]=[CH:5]1

Participants

Conditions

Temperature: 70 °C

Procedure

The product from Step D (1.8 g, 11.0 mmol) was dissolved in 2-methoxyethyl ether (2 mL) and added thionyl chloride (0.89 mL, 12.2 mmol) and pyridine (1 drop) and heated to 70° C. for 24 hours. The mixture was purified by column chromatography (silica gel, 0-15% ethyl acetate/hexanes as an eluent) to provide 5,6-dihydro-4H-benzothiophen-7-one (1.16 g, 72%): 1H NMR (500 MHz, CDCl3) δ 7.61 (d, J=4.9 Hz, 1H), 6.97 (d, J=4.9 Hz, 1H), 2.89-2.87 (m, 2H), 2.63-2.60 (m, 2H), 2.21-2.16 (m, 2H).

Workup

customThe mixture was purified by column chromatography (silica gel, 0-15% ethyl acetate/hexanes as an eluent)

Sources & evidence

ORD record: ord-54b938917b6945f0818ce0d375c7c28c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741901B2

Linked notes

Loading…