Tetrahydrofuran → HCID 22018367, compound

HRID 1368561Notes

Reaction equation

HRID 1368561 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([Mg]Br)[CH:7]=[CH:6]2.[CH:15]([C:17]1[S:21][CH:20]=[N:19][CH:18]=1)=[O:16].[CH2:22]1[CH2:26]OC[CH2:23]1>[Cl-].[NH4+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:15]([C:17]1[S:21][CH:20]=[N:19][CH:18]=1)([OH:16])[CH:22]([CH3:26])[CH3:23])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 27735771,3-Thiazole-5-carbaldehydeHCID 178487536HCID 178487536, compound

Product 1

HCID 22018367HCID 22018367, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 6-methoxynaphthalen-2-ylmagnesium bromide in THF (1.3 M; 10 ml) was added dropwise a solution of 5-formylthiazole (1.70 g) in THF (10 ml) under ice cooling, and the mixture was stirred for 20 min under ice cooling. The mixture was diluted with saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with saturated sodium chloride solution and dried. The solvent was distilled off and the residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=2:1→1:1) to give the titled compound (3.47 g) as a colorless powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-75e54c0d7d1046a3839ee59eae0b5a66
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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