Tetrahydrofuran → HCID 57708916, compound

HRID 546869Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[CH2:24]([C:26]([C:49]1[CH:54]=[CH:53][C:52]([B:55]2[O:59][C:58]([CH3:61])([CH3:60])[C:57]([CH3:63])([CH3:62])[O:56]2)=[C:51]([CH3:64])[CH:50]=1)([C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]2([O:43][Si](C)(C)C)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[C:31]([CH3:48])[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:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)=[C:31]([CH3:48])[CH:30]=1)([C:49]1[CH:54]=[CH:53][C:52]([B:55]2[O:59][C:58]([CH3:60])([CH3:61])[C:57]([CH3:62])([CH3:63])[O:56]2)=[C:51]([CH3:64])[CH:50]=1)[CH2:27][CH3:28])[CH3:25]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 57709030HCID 57709030, compound

Product 1

HCID 57708916HCID 57708916, compoundYield 76.2%

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.95 mL, 0.95 mmol) was added to 2-[4-(1-ethyl-1-{3-methyl-4-[2-(1-trimethylsilanyloxy-cyclohexyl)-ethyl]-phenyl}-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 37-(1); 0.23 g, 0.39 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 (0.15 g, 76%).

Workup

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

Sources & evidence

ORD record: ord-1b39a9b27a6740e9a2f819b4e07bddea
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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