Hydrochloric Acid → HCID 86642979, compound

HRID 888325Notes

Reaction equation

[C:1]1(C)[CH:6]=C[C:4](S(OCCCC#C)(=O)=O)=[CH:3][CH:2]=1.[F:17][C:18]([F:30])([F:29])[CH2:19][CH2:20][S:21]([CH2:24][C:25]([O:27][CH3:28])=[O:26])(=[O:23])=[O:22].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:30][C:18]([F:17])([F:29])[CH2:19][CH2:20][S:21]([CH:24]([CH2:4][CH2:3][CH2:2][C:1]#[CH:6])[C:25]([O:27][CH3:28])=[O:26])(=[O:22])=[O:23]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2.0 g of 4-pentynyl p-toluenesulfonate and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 30 ml of dimethyl sulfoxide, 1.2 g of potassium carbonate was added at room temperature. The mixture was stirred at 60° C. for 4 hours and at 90° C. for 1 hour, and then allowed to stand near room temperature. To the reaction mixture, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.90 g of methyl 2-(3,3,3-trifluoropropylsulfonyl)-6-heptynoate (hereinafter referred to as the present compound (11)).

Workup

customto stand near room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated sodium chloride aqueous solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b59ba2e3636f4cfabb2308e578cb5efe
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247595B2

Reaction notes

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