Trimethylsilyl triflate → Hexamethyldisiloxane

HRID 1623324Notes

Reaction equation

HRID 1623324 reaction equation
CCN(C(C)C)C(C)C.FC(F)(F)S([O:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=O)=O.O1CCC(C=O)CC1>C(Cl)Cl>[CH3:17][Si:16]([O:15][Si:16]([CH3:19])([CH3:18])[CH3:17])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 81531DiisopropylethylamineHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 24764Hexamethyldisiloxane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DIPEA (6.12 mL, 35.0 mmol) in DCM (80 mL) was added trimethylsilyl trifluoromethanesulfonate (7.79 g, 35.0 mmol) followed by a solution of tetrahydro-2H-pyran-4-carbaldehyde (2 g, 17.52 mmol) in DCM (80 mL) at 0° C. Upon completion of the addition, the reaction mixture was allowed to stir at ambient temperature for 2 hr. The mixture was concentrated in vacuo and the resulting residue was treated with hexane (200 mL). The precipitate was filtered off and the solution was concentrated in vacuo providing crude trimethylsilyl ether, which was directly used in the next step without further purification.

Workup

  1. additionUpon completion of the addition
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe resulting residue was treated with hexane (200 mL)
  4. filtrationThe precipitate was filtered off
  5. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-117fb2fea6d24a309365d98e14350dc6
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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