1-Octanol → HCID 178443704, compound

HRID 1780564Notes

Reaction equation

HRID 1780564 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([C:36]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[C:46]([F:48])[C:45]([OH:49])=[CH:44][CH:43]=2)=[C:38]([O:50][SiH:51]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:37]=1)([CH3:35])([CH3:34])[CH3:33].[CH2:64](O)[CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71]>O1CCCC1>[C:32]([C:36]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[C:46]([F:48])[C:45]([O:49][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])=[CH:44][CH:43]=2)=[C:38]([O:50][SiH:51]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH:37]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1784407546-(4-tert-butyl-2-diphenylsilyloxyphenyl)-2-fluoropyridin-3-ol

Product 1

HCID 178443704HCID 178443704, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.30 g (13.35 mmol) of diethyl azodicarboxylate are added dropwise at 0° C. to 3.47 g (13.35 mmol) of triphenylphosphine in 100 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 30 minutes. 3.58 g (8.10 mmol) of 6-(4-tert.-butyldiphenylsilyloxyphenyl)-2-fluoro-3-hydroxypyridine and 1.70 g (13.35 mmol) of 1-octanol are then added. After a reaction time of 1.5 hours at room temperature, the solvent is distilled off, and the residue is purified by chromatography (silica gel, 95:5 hexane/ethyl acetate), giving 4.43 g of 6-(4-tert.-butyldiphenylsilyloxyphenyl)-2-fluoro-3-octyloxypyridine. ##STR46##

Workup

  1. distillationAfter a reaction time of 1.5 hours at room temperature, the solvent is distilled off
  2. customthe residue is purified by chromatography (silica gel, 95:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2a10a29f7a70411cb32fc46af08fe207
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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