Ammonium Chloride → (3-Benzyloxy-4-nitrophenyl)-thiazol-2-yl-methanol

HRID 660739Notes

Reaction equation

HRID 660739 reaction equation
[Li]CCCC.Br[C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[CH:23]=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].[Cl-]>CCOCC.C1COCC1>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([CH:23]([C:7]2[S:8][CH:9]=[CH:10][N:11]=2)[OH:24])[CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 764302-BromothiazoleHCID 12111719HCID 12111719, compoundHCID 178418339Butyllithium

Product 1

HCID 68842524(3-Benzyloxy-4-nitrophenyl)-thiazol-2-yl-methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of n-BuLi (1.9 mL, 2.5 M in hexane) in ether (8 mL) at −78° C. is added 2-bromothiazole (0.34 mL, 3.80 mmol) dropwise. The yellow solution is stirred at −78° C. for 30 min and 3-benzyloxy-4-nitrobenzaldehyde (83, step A) (0.81 g, 3.16 mmol) in THF (2 mL) is added. After stirring for 30 min, the purple suspension is poured into a sat. NH4Cl solution (50 mL) and is extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4 and concentrated. The residue is then purified by column chromatography to give the title compound: (M+1)+=343.

Workup

  1. stirringAfter stirring for 30 min
  2. extractionis extracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is then purified by column chromatography

Sources & evidence

ORD record
ord-99158122bac243588c0c01e042708627
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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