Octanal → HCID 15232556, compound

HRID 1109792Notes

Reaction equation

[CH3:1][C:2]([NH:6][S:7]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8])([CH3:5])[C:3]#[CH:4].C([Mg]Br)C.[CH:21](=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O>C1COCC1>[OH:29][CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:4]#[C:3][C:2]([CH3:1])([NH:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]([CH3:14])=[CH:15][CH:16]=1)(=[O:8])=[O:9])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

In 2 ml of THF was dissolved 1.185 g (5 mmole) of 3-methyl-3-tosylamino-1-butyne, and a THF solution of ethylmagnesium bromide (12 mmole) was added thereto at room temperature, followed by refluxing for 1 hour. After cooling the solution to 0° C., a solution of 1.25 ml (8 mmole) of n -octanal in 3 ml of THF was added thereto, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with a hydrochloric acid aqueous solution, a sodium hydrogencarbonate aqueous solution, and water, and then dried. The solvent was removed by distillation, and the residual oily substance was purified by column chromatography to obtain 1.37 g (percent yield: 75%) of 5-hydroxy-2-methyl-2-tosylamino-3-dodecyne.

Workup

customat room temperature
temperatureby refluxing for 1 hour
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed successively with a hydrochloric acid aqueous solution
dry with materiala sodium hydrogencarbonate aqueous solution, and water, and then dried
customThe solvent was removed by distillation
customthe residual oily substance was purified by column chromatography

Sources & evidence

ORD record: ord-f7b3be53d5bd48848f3a029d6704a8da
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05322939

Reaction notes

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