Water → 5,9-Dimethyl-9-triethylsilanyloxy-decanal

HRID 493070Notes

Reaction equation

HRID 493070 reaction equation
[OH:1][C:2]([CH3:14])([CH3:13])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH:10]=[O:11].N1C(C)=CC=CC=1C.[Si:23](OS(C(F)(F)F)(=O)=O)([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25].O>C(Cl)Cl>[CH3:12][CH:6]([CH2:5][CH2:4][CH2:3][C:2]([CH3:13])([O:1][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH3:14])[CH2:7][CH2:8][CH2:9][CH:10]=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 218389029-Hydroxy-5,9-dimethyl-decanal

Product 1

HCID 765908305,9-Dimethyl-9-triethylsilanyloxy-decanalYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

To a solution of aldehyde 15 (16.5 mg, 82.5 μmol) and 2,6-lutidine (24 μL, 206 ,μmol) in anhydrous CH2Cl2 (1.1 mL) was added dropwise Et3SiOTf (42 μL, 165 μmol) at −78° C. The mixture was stirred for 2 hours at −78° C. and for one additional hour at −50° C. Water and CH2Cl2 were added, the organic layer was washed with water, dried over MgSO4, and evaporated. The residue was chromatographed on silica Sep-Pak cartridge using hexane/EtOAc (99.7:0.3) as an eluent to give oily aldehyde 16 (22 mg, 85%). An analytical sample was obtained using HPLC (10 mm ×25 cm Zorbax-Sil column, 4 mL/min) with a hexane/EtOAc (98:2) solvent system. Analytically pure aldehyde 16 was collected at Rv=33 mL.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was chromatographed on silica Sep-Pak cartridge

Sources & evidence

ORD record
ord-9ea71e8060704472b2c7f14a877b3d50
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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