tert-Butyldimethylsilyl chloride → HCID 22406954, compound

HRID 440323Notes

Reaction equation

HRID 440323 reaction equation
C[C:2]([Si:5](Cl)([CH3:7])[CH3:6])(C)C.C1CCN2C(=NCCC2)CC1.[OH:20][CH:21]([C:27]1[S:28][CH:29]=[CH:30][N:31]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[CH3:2][Si:5]([CH3:7])([CH3:6])[O:20][CH:21]([C:27]1[S:28][CH:29]=[CH:30][N:31]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15785703HCID 15785703, compound

Product 1

HCID 22406954HCID 22406954, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBDMSCl (1.37 g, 9.07 mmol) and DBU (1.4 mL, 9.07 mmol) were added to a solution of 2-(1-hydroxyhexyl)thiazole (0.7 g, 3.8 mmol) in dry THF (8 mL). The mixture was stirred at rt for 3 h, then quenched with water and the layers separated. The aqueous portion was extracted with EtOAc, the combined extracts dried (MgSO4) and concentrated. The material was purified by flash chromatography to give 1.03 g (91%) of 2-(1-trimethylsiloxyhexyl)thiazole as a pale yellow oil.

Workup

  1. customquenched with water
  2. customthe layers separated
  3. extractionThe aqueous portion was extracted with EtOAc
  4. dry with materialthe combined extracts dried (MgSO4)
  5. concentrationconcentrated
  6. customThe material was purified by flash chromatography

Sources & evidence

ORD record
ord-da422fd4da8d47efa8dc71b603c738f9
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

Loading…