Hydrochloric Acid → Methyl 2-(3,3,3-trifluoropropylsulfonyl)-7-octynoate

HRID 888323Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[CH:7].[F:8][C:9]([F:21])([F:20])[CH2:10][CH2:11][S:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:14])=[O:13].[H-].[Na+].Cl>CS(C)=O>[F:21][C:9]([F:8])([F:20])[CH2:10][CH2:11][S:12]([CH:15]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]#[CH:2])[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1.0 g of 6-chloro-1-hexyne and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide, 0.3 g of sodium hydride (60% in oil) was added at room temperature. The mixture was stirred at room temperature for 12 hours, at 60° C. for 2 hours and then at 90° C. for 10 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 1.50 g of methyl 2-(3,3,3-trifluoropropylsulfonyl)-7-octynoate (hereinafter referred to as the present compound (1)).

Workup

waitat 90° C. for 10 hours
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-d43020439d0c47cfa61e1fbd7b40545f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247595B2

Reaction notes

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