Triphenylphosphine → 1-[4-(6-Fluoro-5-octylpyrazin-2-yl)phenoxy]octan-4-yl-dimethylsilane

HRID 864272Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=CC=C[CH:14]=1.[F:32][C:33]1[C:38]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[N:37][CH:36]=[C:35]([C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)[N:34]=1.[CH2:54]([CH2:58][CH2:59][CH2:60][CH:61]([SiH:63]([CH3:65])[CH3:64])O)CCC>O1CCCC1>[F:32][C:33]1[C:38]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[N:37][CH:36]=[C:35]([C:47]2[CH:48]=[CH:49][C:50]([O:53][CH2:14][CH2:13][CH2:18][CH:61]([SiH:63]([CH3:64])[CH3:65])[CH2:60][CH2:59][CH2:58][CH3:54])=[CH:51][CH:52]=2)[N:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.82 ml (11.60 mmol) of diethyl azodicarboxylate are added dropwise at 0° C. to 3.04 g (11.60 mmol) of triphenylphosphine in 85 ml of tetrahydrofuran, and this mixture is stirred at 0° C. for 0.5 hour. 2.00 g (7.00 mmol) of 2-fluoro-3-octyl-6-(4-hydroxyphenyl)-pyrazine (prepared as described in Example 4a to 4d) and 2.46 g (11.60 mmol) of 4-butyldimethylsilylbutanol are subsequently added, and the mixture is stirred at room temperature for 3 hours. The reaction mixture is evaporated, and the residue is purified by chromatography (silica gel/dichloromethane: hexane = 8:2). 1.47 g of 2-fluoro-3-octyl-6-[4-(4-butyldimethylsilylbutyloxy)-phenyl-]pyrazine are obtained. ##STR27##

Workup

stirringthe mixture is stirred at room temperature for 3 hours
customThe reaction mixture is evaporated
customthe residue is purified by chromatography (silica gel/dichloromethane: hexane = 8:2)

Sources & evidence

ORD record: ord-4b36ba47ebbc4359bbcd8d43daffecdb
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05562859

Reaction notes

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