Tetrabutylammonium Fluoride → HCID 86759394, compound

HRID 49370Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:34]=1[CH2:35][O:36][Si](C(C)(C)C)(C)C)[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:30][CH3:31])=[CH:21]/[CH:22]=[CH:23]/[C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])[CH:16]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:34]=1[CH2:35][OH:36])[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:30][CH3:31])=[CH:21]/[CH:22]=[CH:23]/[C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])[CH:16]=1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 88011758HCID 88011758, compound

Product 1

HCID 86759394HCID 86759394, compound

Procedure

In a manner similar to that of Example 7(f), by reaction of 155 mg (0.24 mmol) of (4E,6E)-7-{5-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}-3-ethylnona-4,6-dien-3-ol with 0.58 mL (0.58 mmol) of 1 M tetrabutylammonium fluoride solution, (4E,6E)-7-[5-(3,4-bis-hydroxymethyl-phenoxymethyl)-3-thienyl]-3-ethylnona-4,6-dien-3-ol is obtained in the form of a yellow oil (m=80 mg; Y=80%).

Sources & evidence

ORD record: ord-2ec0c8c503174258a53342a7c9e59b0f
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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