2,6-Lutidine → HCID 59563750, compound

HRID 1944169Notes

Reaction equation

HRID 1944169 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[Si:27](OS(C(F)(F)F)(=O)=O)([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29]>C(Cl)Cl>[CH:28]([Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[CH:6][CH:7]=1)([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Product 1

HCID 59563750HCID 59563750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To benzyl 2-(4-hydroxyphenyl)acetate (E301) in CH2Cl2 at 0° C. was added 2,6-lutidine and TIPS-OTf and the solution stirred for 2.5 h at 0° C. The mixture was poured into NH4Cl(sat) and extracted with CH2Cl2. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 0-15% EtOAc/Hex) gave pure benzyl 2-(4-(triisopropylsiloxy)phenyl)acetate (E302).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-84a72d5834024a76bedb9b50546b53d2
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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