2,6-Lutidine → Methyl 2-(4-((triisopropylsilyloxy)methyl)phenyl)acetate

HRID 1020092Notes

Reaction equation

HRID 1020092 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.N1C(C)=CC=CC=1C.[Si:22](OS(C(F)(F)F)(=O)=O)([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24]>C(Cl)Cl>[CH:23]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 12575321Methyl 2-[4-(hydroxymethyl)phenyl]acetate

Product 1

HCID 59563736Methyl 2-(4-((triisopropylsilyloxy)methyl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 2-(4-(hydroxymethyl)phenyl)acetate (E132) in CH2Cl2 at 0° C. was added 2,6-lutidine and TIPS-OTf. The ice bath was removed and the solution was allowed to warm to room temperature and stir. After 4 h the solution was poured into NH4Cl(sat) and CH2Cl2 and the organic layer was further extracted with NH4Cl(sat). The organics were dried (MgSO4) filtered and evaporated. Column chromatography (SiO2, 0-15% EtOAc/Hexanes) gave pure methyl 2-(4-((triisopropylsilyloxy)methyl)phenyl)acetate (E133).

Workup

  1. customThe ice bath was removed
  2. additionAfter 4 h the solution was poured into NH4Cl(sat) and CH2Cl2
  3. extractionthe organic layer was further extracted with NH4Cl(sat)
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-79b2d6083add483480810ae43f6ad18a
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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