Tetrabutylammonium Fluoride → 7-[4-(4-Methoxyphenyl)thiazol-2-yl]heptan-1-ol

HRID 1039149Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[S:35][CH:36]=[C:37]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[N:38]=1)(C(C)(C)C)(C)C>C1COCC1.[Cl-].[Na+].O>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([C:37]2[N:38]=[C:34]([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][OH:26])[S:35][CH:36]=2)=[CH:44][CH:43]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Add a solution of 1 N tetra-n-butylammonium fluoride (25.0 mmol, 25 mL, 1 M solution in THF) dropwise over 10 minutes to a solution of 2-[7-(tert-butyldimethylsilanyloxy)heptyl]-4-(4-methoxyphenyl)thiazole (6.27 g, 14.9 mmol) in anhydrous THF (50 mL) at 0° C. under nitrogen and stir the mixture for 30 minutes at 0° C. and then stir at room temperature for 3 hours. Dilute the mixture with brine (150 mL) and extract with ethyl acetate (100 mL×3). Dry the combined organic extracts over magnesium sulfate and remove the solvent under reduced pressure. Purify the crude product by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:2), to give 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptan-1-ol (4.07 g, 89%): APCI mass spectrum m/z 306 [C17H23NO2S+H]+.

Workup

stirringstir at room temperature for 3 hours
extractionextract with ethyl acetate (100 mL×3)
dry with materialDry the combined organic extracts over magnesium sulfate
customremove the solvent under reduced pressure
customPurify the crude product by flash column chromatography on silica gel
washeluting with ethyl acetate/hexanes (1:2)

Sources & evidence

ORD record: ord-b4f2fb1e1ed5484ea13286eb909cf934
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552039B2

Reaction notes

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