Hydrochloric Acid → HCID 86642980, compound

HRID 888326Notes

Reaction equation

[C:1]1([CH3:18])[CH:6]=[CH:5][C:4](S(OCCCCCC#C)(=O)=O)=[CH:3][CH:2]=1.[F:19][C:20]([F:32])([F:31])[CH2:21][CH2:22][S:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])(=[O:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:32][C:20]([F:19])([F:31])[CH2:21][CH2:22][S:23]([CH:26]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]#[CH:18])[C:27]([O:29][CH3:30])=[O:28])(=[O:24])=[O:25]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3.0 g of 6-heptynyl p-toluenesulfonate and 2.6 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide, 1.6 g of potassium carbonate was added at room temperature. The mixture was heated to 90° C. and stirred at the same temperature for 6 hours. The reaction mixture was allowed to stand near room temperature, and 10% hydrochloric acid was added thereto, 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 0.80 g of methyl 2-(3,3,3-trifluoropropylsulfonyl)-8-nonynoate (hereinafter referred to as the present compound (14)).

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-a61fce26abcd4a97b668f96830a9bb80
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247595B2

Reaction notes

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