2,6-Lutidine → HCID 86714069, compound

HRID 576378Notes

Reaction equation

HRID 576378 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:18][O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[OH:9])[CH:7]=1.N1C(C)=CC=CC=1C.[Si:38](OS(C(F)(F)F)(=O)=O)([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:18][O:19][Si:20]([CH:21]([CH3:22])[CH3:23])([CH:27]([CH3:28])[CH3:29])[CH:24]([CH3:26])[CH3:25])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[O:9][Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[CH:7]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 86714070HCID 86714070, compound

Product 1

HCID 86714069HCID 86714069, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 4) To a solution of (5-bromo-2-((triisopropylsilyloxy)methyl)phenyl)(4-ethylphenyl)methanol (4.76 mmol) and 2,6-lutidine (1.6 mL, 13.51 mmol) in dichloromethane (30.0 mL) was slowly added TIPSOTf (1.8 mL, 6.75 mmol) at 0° C., and the reaction mixture was stirred for 12 h at room temperature. The resulting mixture was quenched with CH3OH, diluted with EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude was purified by silica gel column chromatography to provide the title compound (2.94 g, 97% 2-step) as yellow oil.

Workup

  1. customat 0° C.
  2. customThe resulting mixture was quenched with CH3OH
  3. additiondiluted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-19ea384e02bc48088f0774320d238b37
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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