Tetrahydrofuran → HCID 57709074, compound

HRID 546864Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[CH2:24]([C:26]([C:48]1[CH:53]=[CH:52][C:51]([B:54]2[O:58][C:57]([CH3:60])([CH3:59])[C:56]([CH3:62])([CH3:61])[O:55]2)=[C:50]([CH3:63])[CH:49]=1)([C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]2([O:42][Si](C)(C)C)[CH2:41][CH2:40][CH2:39][CH2:38]2)=[C:31]([CH3:47])[CH:30]=1)[CH2:27][CH3:28])[CH3:25]>>[CH2:24]([C:26]([C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]2([OH:42])[CH2:38][CH2:39][CH2:40][CH2:41]2)=[C:31]([CH3:47])[CH:30]=1)([C:48]1[CH:53]=[CH:52][C:51]([B:54]2[O:58][C:57]([CH3:59])([CH3:60])[C:56]([CH3:61])([CH3:62])[O:55]2)=[C:50]([CH3:63])[CH:49]=1)[CH2:27][CH3:28])[CH3:25]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 577089962-[4-(1-Ethyl-1-{3-methyl-4-[2-(1-trimethylsilanyloxy-cyclopentyl)-ethyl]-phenyl}-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 57709074HCID 57709074, compoundYield 53%

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.33 mL, 1.33 mmol) was added to 2-[4-(1-ethyl-1-{3-methyl-4-[2-(1-trimethylsilanyloxy-cyclopentyl)-ethyl]-phenyl}-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 34-(1); 0.25 g, 0.48 mmol), and the mixture was stirred for three hours. The reaction mixture was purified by silica gel chromatography (14% ethyl acetate/hexane) to give the title compound (0.12 g, 53%).

Workup

customThe reaction mixture was purified by silica gel chromatography (14% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-ffdf6f61d970446394ee99349c0d0019
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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