Triethylamine → 4-[3-(tert-Butyldimethylsilanyloxy)propyl]oxazole

HRID 1096818Notes

Reaction equation

HRID 1096818 reaction equation
[O:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][OH:9])[N:3]=[CH:2]1.CCN(CC)CC.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl>[Si:21]([O:9][CH2:8][CH2:7][CH2:6][C:4]1[N:3]=[CH:2][O:1][CH:5]=1)([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 667834654-Oxazolepropanol

Product 1

HCID 667838214-[3-(tert-Butyldimethylsilanyloxy)propyl]oxazoleYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a sol. of 3-oxazol-4-yl-propan-1-ol (1.14 g, 8.96 mmol) in dry CH2Cl2 (25 mL) at 0° C. were added Et3N (3.12 mL, 22.4 mmol) and TBDMS-Cl (2.02 g, 13.4 mmol). The reaction mixture was stirred at rt overnight, and the mixture was concentrated under reduced pressure. The residue was diluted in Et2O, and the mixture was washed with water. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/Et2O; 30:1→1:1) yielded the title compound (1.84 g, 85%). LC-MS: tR=1.06, ES+: 242.28.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted in Et2O
  3. washthe mixture was washed with water
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (heptane/Et2O; 30:1→1:1)

Sources & evidence

ORD record
ord-20aaa7d101204993833c5404ec08108a
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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