2,6-Lutidine → 1-Benzyloxymethyl-5-[(3-benzyloxy-4-nitrophenyl)-(tert-butyldimethylsilanyloxy)-methyl]-1h-pyrazole

HRID 660742Notes

Reaction equation

HRID 660742 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:18]=2)[OH:16])=[CH:13][CH:12]=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:34](OS(C(F)(F)F)(=O)=O)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].N1C(C)=CC=CC=1C>C(Cl)Cl>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:18]=2)[O:16][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])=[CH:13][CH:12]=[N:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 68839814HCID 68839814, compound

Product 1

HCID 688377751-Benzyloxymethyl-5-[(3-benzyloxy-4-nitrophenyl)-(tert-butyldimethylsilanyloxy)-methyl]-1h-pyrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-benzyloxymethyl-2H-pyrazol-3-yl)-(3-benzyloxy-4-nitrophenyl)-methanol (392 mg, 0.881 mmol), TBSOTf (0.25 mL, 1.09 mmol) and 2,6-lutidine (0.153 mL, 1.32 mmol) in CH2Cl2 is stirred at RT for 2 h. The mixture is partitioned between CH2Cl2 and aqueous NaHCO3. The organic phase is dried over MgSO4 and concentrated. The residue is purified by flash chromatography to give the title compound.

Workup

  1. customThe mixture is partitioned between CH2Cl2 and aqueous NaHCO3
  2. dry with materialThe organic phase is dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-4ef4566faecf4aaeb0e4634ae51ad5ce
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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