Chloride → HCID 86746132, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-dithiane (1.55 g, 12.9 mmole) in tetrahydrofuran (60 ml) cooled to -30° C. was added dropwise a 1.32M solution of n-butyllithium in hexane (9.77 ml, 12.9 mmoles), the mixture was stirred at -30° C. for 30 min. Then the mixture was cooled to -40° C. and the chloride prepared in 1C (2.69 g, 12.9 mmoles) in tetrahydrofuran (10 ml) was added dropwise. The reaction was stirred 30 min at -40° C. and 2 hrs at 0° C. The reaction was quenched with saturated aqueous ammonium chloride and the tetrahydrofuran was evaporated under reduced pressure. The residue was diluted with ether and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography on silicagel and elution with a 8:2 mixture of hexane and ethyl acetate afforded the title dithialane as an oil (3.34 g, 90%). NMR (H1, CDCl3, 60 MHz) characetristic peaks: 4.00 (t, JHH =7 Hz, 1), 4.21 (d, JHF =20 Hz, 2), 4.7 (broad peak, 1), 5.40 (dt, JHF =20 Hz, JHH =8 Hz, 1).

Provenance & Evidence