Hydrochloric Acid → HCID 21917840, compound

HRID 1244188Notes

Reaction equation

CC1(C)CCCC(C)(C)N1.C([Li])CCC.CCCCCC.[F:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([I:30])[CH:24]=1.[CH2:31]([CH:34]1[CH2:39][CH2:38][CH:37]([CH:40]2[CH2:45][CH2:44][CH:43](C=CC=O)[CH2:42][CH2:41]2)[CH2:36][CH2:35]1)[CH2:32][CH3:33].Cl.[O:51]1C[CH2:54][CH2:53][CH2:52]1>O>[F:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([I:30])[C:24]=1[CH:52]([OH:51])[C:53]([CH:43]1[CH2:44][CH2:45][CH:40]([CH:37]2[CH2:38][CH2:39][CH:34]([CH2:31][CH2:32][CH3:33])[CH2:35][CH2:36]2)[CH2:41][CH2:42]1)=[CH2:54]

Participants

Conditions

Temperature: -20 °C

Procedure

An initial charge of 31.1 g (0.22 mol) of 2,2,6,6-tetramethylpiperidine in 350 ml of tetrahydrofuran is cooled down to −20° C. 135 ml of 1.6 M butyllithium in hexane (0.22 mol) are added dropwise at this temperature. The mixture is cooled down to -18° C. and 47.2 g (0.2 mol) of 1-fluoro-3-iodo-5-methylbenzene are added dropwise at this temperature. The reaction mixture is stirred for another hour at −80° C. and then treated with 52.5 g (0.2 mol) of 3-(4′-propylbicyclohexyl-4-yl)propenal. The mixture is allowed to warm to 0° C., hydrolyzed with water and diluted hydrochloric acid and then subjected to conventional work-up.

Workup

temperatureThe mixture is cooled down to -18° C.

Sources & evidence

ORD record: ord-8c5ad5f1b9994bde8fd04dcdb6f23f89
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122228B2

Reaction notes

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