Tetrabutylammonium Fluoride → (4E,6E)-7-(4-{2-[3,4-bis-hydroxymethyl-phenyl]ethyl}-2-thienyl)-3-ethylnona-4,6-dien-3-ol

HRID 49371Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:32](/[CH2:42][CH3:43])=[CH:33]/[CH:34]=[CH:35]/[C:36]([CH2:40][CH3:41])([OH:39])[CH2:37][CH3:38])[S:30][CH:31]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][O:17][Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:32](/[CH2:42][CH3:43])=[CH:33]/[CH:34]=[CH:35]/[C:36]([CH2:40][CH3:41])([OH:39])[CH2:37][CH3:38])[S:30][CH:31]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][OH:17]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 88012102HCID 88012102, compound

Product 1

HCID 86759396(4E,6E)-7-(4-{2-[3,4-bis-hydroxymethyl-phenyl]ethyl}-2-thienyl)-3-ethylnona-4,6-dien-3-ol

Procedure

In a manner similar to that of Example 7(f), by reaction of 440 mg (0.68 mmol) of (4E,6E)-7-(4-{2-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl]ethyl}-2-thienyl)-3-ethylnona-4,6-dien-3-ol with 1.5 mL (1.5 mmol) of 1 M tetrabutylammonium fluoride solution, (4E,6E)-7-(4-{2-[3,4-bis-hydroxymethyl-phenyl]ethyl}-2-thienyl)-3-ethylnona-4,6-dien-3-ol is obtained in the form of a yellow oil (m=200 mg; Y=71%).

Sources & evidence

ORD record: ord-85e39a087e5047119543f805f021ae76
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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