2,6-Lutidine → Methyl 4-(triisopropylsiloxy)phenylacetate

HRID 1020085Notes

Reaction equation

HRID 1020085 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[Si:21](OS(C(F)(F)F)(=O)=O)([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23]>C(Cl)Cl>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 10471397Methyl 4-(triisopropylsiloxy)phenylacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 2-(4-hydroxyphenyl)acetate (E1) 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 stirred. 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 (Na2SO4) filtered and evaporated. Column chromatography (0-15% EtOAc/Hexanes) gave pure methyl-2-(4-(triisopropylsilyloxy)phenyl)acetate (E2).

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 (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4c3a97eb515247c7948b1af878b15bca
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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