Triethylamine → HCID 21844643, compound

HRID 1738624Notes

Reaction equation

HRID 1738624 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH:10]([OH:12])[CH2:9][CH2:8][CH2:7]1)=[O:2].CCN(CC)CC.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]([CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH:10]([O:12][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:9][CH2:8][CH2:7]1)=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 21844652HCID 21844652, compound

Product 1

HCID 21844643HCID 21844643, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 25 mL round bottomed flask was placed a solution of 6-(3-formylpropyl)-2-hydroxytetrahydropyran (153 mg, 0.89 mmol), DMAP (5 mg), and Et3N (0.4 mL) in CH2Cl2 (10 mL). The solution was cooled to 0° C., and tert-butyldimethylsilyl chloride (205 mg, 1.34 mmol) in CH2Cl2 (3 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight, and then the solvent was removed under reduced pressure. Ether was added and the organic layer was washed with saturated NH4Cl twice followed by brine, dried over anhydrous magnesium sulfate, and then concentrated in vacuo. The residue was submitted to column chromatography on silica gel to afford 6-(3-formylpropyl)-2-(tert-butyldimethylsiloxy)tetrahydropyran as a clear yellow oil (206 mg, 90% yield): 1H NMR (CDCl3) δ 0.09 (s, 3H), 0.10 (s, 3H), 0.89 (s, 9H), 1.19-1.73 (m, 10H), 2.43 (m, 2H), 3.34 (t, 1H, J=5.7 Hz), 4.63 (d, 1H, J=9 Hz), 9.74 (s, 1H); 13C NMR (CDCl3) δ -4.0, 18.14, 18.41, 22.21, 25.81, 30.61, 33.83, 35.25, 43.70, 75.70, 97.26, 202.63. HRMS [CI (CH4)] calcd for C15H29O3Si: 285.1886 (M-H,)+. Found: 285.1890 (Δ-1.4 ppm).

Workup

  1. customIn a 25 mL round bottomed flask was placed
  2. temperatureto warm to room temperature overnight
  3. customthe solvent was removed under reduced pressure
  4. additionEther was added
  5. washthe organic layer was washed with saturated NH4Cl
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-243e160641584dbda79ae6354b51a544
Source dataset
uspto-grants-1999_10
Patent number
US05962744

Reaction notes

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