Tetrabutylammonium Fluoride → (e)-7-{4-[2-(3,4-Bis-hydroxymethyl-phenyl)ethyl]-2-thienyl}-3-ethylnon-6-en-3-ol

HRID 49355Notes

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]/[CH2:34][CH2:35][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]/[CH2:34][CH2:35][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 69825578(E)-7-{4-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-3-ethylnon-6-en-3-ol

Product 1

HCID 69824840(e)-7-{4-[2-(3,4-Bis-hydroxymethyl-phenyl)ethyl]-2-thienyl}-3-ethylnon-6-en-3-ol

Procedure

In a manner similar to that of Example 6(l), by reaction of 1 g (1.55 mmol) of (E)-7-{4-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-3-ethylnon-6-en-3-ol with 3.7 mL (3.7 mmol) of 1.0 M tetrabutylammonium fluoride solution, the desired product is obtained in the form of white crystals (m.p.=85-86° C.; m=580 mg; Y=90%).

Sources & evidence

ORD record: ord-51950856c16743d3907bedb416235762
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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