Hydrochloric Acid → HCID 67401804, compound

HRID 1186400Notes

Reaction equation

HRID 1186400 reaction equation
C([Li])CCC.CCCCCC.Br[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[S:19]1[C:23]([CH:24]=[O:25])=[CH:22][N:21]=[CH:20]1.Cl>O1CCCC1.C1(C)C=CC=CC=1>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:24]([C:23]2[S:19][CH:20]=[N:21][CH:22]=2)[OH:25])[CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 122863-BromopyridineHCID 27735771,3-Thiazole-5-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 67401804HCID 67401804, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

According to Reference Example 8-68, a 1.55 mol/L solution of n-butyllithium in hexane (2.24 mL, 3.48 mmol) was added to toluene (6 mL), and the mixture was stirred with a toluene solution (2 mL) of 3-bromopyridine (500 mg, 3.16 mmol), tetrahydrofuran (2 mL), thiazole-5-carbaldehyde (0.329 mL, 3.79 mmol) and 4 mol/L hydrochloric acid (2.37 mL, 9.48 mmol). Then, purification by preparative thin-layer chromatography (chloroform/methanol=12/1) was performed to give pyridin-3-yl(thiazol-5-yl)methanol (Compound EQ) (271 mg, yield: 45%).

Workup

  1. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=12/1)

Sources & evidence

ORD record
ord-99327a5c6d6049eca0801318db94a51e
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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