Potassium Iodide → 6-Trifluoromethylsulphonyl-2,2-dimethyl-2H-benzo(b)pyran

HRID 1086316Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[C:24]([CH3:28])([CH3:27])[C:25]#[CH:26]>CC(=O)CC>[F:14][C:2]([F:13])([F:1])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:12][C:24]([CH3:28])([CH3:27])[CH:25]=[CH:26][C:10]=2[CH:11]=1)(=[O:4])=[O:5]

Participants

Conditions

Temperature: 180 °C

Procedure

1 g (4.4 mmol) of 4-trifluoromethylsulphonylphenol are stirred under argon at 80°-90° C. for 20 hours together with 0.66 g of potassium carbonate, 80 mg of potassium iodide and 2 g of 3-chloro-3-methyl-1-butyne in 13 ml of dry butanone. 0.33 g of potassium carbonate, 40 mg of potassium iodide and 1 g of 3-chloro-3-methyl-1-butyne are then added once again and the mixture is stirred at 80°-90° C. for a further 20 hours. It is then allowed to cool and is filtered, and the filtrate is evaporated. The residue is taken up in 20 ml of methylene chloride, washed with water (2×20 ml), dried and evaporated. The oil which remains (1.3 g) is heated under argon to 180° C. for 3 hours in o-dichlorobenzene (3 ml). After distilling off the solvent, the residue is chromatographed on silica gel. 0.5 g of colorless oil are obtained (50 % of theory). M+ =292 (5).

Workup

temperatureto cool
filtrationis filtered
customthe filtrate is evaporated
washwashed with water (2×20 ml)
customdried
customevaporated
distillationAfter distilling off the solvent
customthe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-18eb613b8aa445dbbbb1df7cf5be1768
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05028711

Reaction notes

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