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

HRID 486865Notes

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-3e297f53656b47deb20b8cefb6f43d35
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292911

Reaction notes

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