Hydrochloric Acid → 15-Chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13 pentadecatetraenenitrile

HRID 892640Notes

Reaction equation

[Cl:1][CH2:2][C:3]([CH3:28])=[CH:4][CH2:5][CH2:6][C:7]([CH3:27])=[CH:8][CH2:9][CH2:10][C:11]([CH3:26])=[CH:12][CH:13]=[C:14]([CH:23]([CH3:25])[CH3:24])[CH:15]([O:18][Si](C)(C)C)[C:16]#[N:17].Cl>O1CCCC1>[Cl:1][CH2:2][C:3]([CH3:28])=[CH:4][CH2:5][CH2:6][C:7]([CH3:27])=[CH:8][CH2:9][CH2:10][C:11]([CH3:26])=[CH:12][CH:13]=[C:14]([CH:23]([CH3:24])[CH3:25])[CH:15]([OH:18])[C:16]#[N:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 15-chloro-3-(1-methylethyl)-6,10, 14-trimethyl-2-trimethylsiloxy-3,5,9,13-pentadecatetraenenitrile (58 mg, 0.14 mmol) prepared in Reference Example 5 in tetrahydrofuran (2 ml) cooled at 0° C. is slowly added 1N hydrochloric acid (0.5 ml). After stirring at this temperature for 10 minutes, to the mixture is added a saturated saline solution (5 ml) and the mixture is extracted with ether (10 ml×2). The organic layer is washed with a saturated saline solution (5 ml) and dried over anhydrous sodium sulfate. The solvent is removed by distillation under reduced pressure and the resulting residue is purified by silica gel column chromatography (n-hexane/ethyl acetate =10:1) to give 15-chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile (38 mg, 75%).

Workup

extractionthe mixture is extracted with ether (10 ml×2)
washThe organic layer is washed with a saturated saline solution (5 ml)
dry with materialdried over anhydrous sodium sulfate
customThe solvent is removed by distillation under reduced pressure
customthe resulting residue is purified by silica gel column chromatography (n-hexane/ethyl acetate =10:1)

Sources & evidence

ORD record: ord-7ef8a76e954e4791bd005e9af1e2363a
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05118827

Reaction notes

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