Dichloromethane → HCID 68412077, compound

HRID 2400272Notes

Reaction equation

HRID 2400272 reaction equation
N1C(C)=CC=CC=1C.C(Cl)Cl.[OH:12][C:13]([CH3:26])([CH3:25])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].FC(F)(F)S(O[Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])(=O)=O>C(OCC)(=O)C>[Si:33]([O:12][C:13]([CH3:26])([CH3:25])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 13981853HCID 13981853, compound

Product 1

HCID 68412077HCID 68412077, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,6-Lutidine (3.6g) was added to an anhydrous methylene chloride solution of benzyl 3-hydroxy-3-methylbutyrate (3.5g) obtained in the step 1, and stirred with cooling with ice. t-butyldimethylsilyl trifluoromethanesulfonate (3.9mL) was gradually added dropwise thereto, and stirred for 1hour with cooling on ice and then for 2hours at room temperature. The reaction liquid was diluted with ethyl acetate, then washed with water, aqueous saturated ammonium chloride solution and aqueous saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and concentrated. 4.5g of the residue was purified through silica gel column chromatography to give benzyl 3-(t-butyldimethylsilyloxy)-3-methylbutyrate (2.62g) as a colorless oil.

Workup

  1. customobtained in the step 1
  2. temperaturewith cooling with ice
  3. stirringstirred for 1hour
  4. temperaturewith cooling on ice
  5. customThe reaction liquid
  6. washwashed with water, aqueous saturated ammonium chloride solution and aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. custom4.5g of the residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-d95339e0cec5445bb7d4ea97ec0a8d21
Source dataset
uspto-grants-2014_08
Patent number
US08796246B2

Reaction notes

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