tert-Butyldimethylsilyl chloride → HCID 53920845, compound

HRID 440326Notes

Reaction equation

HRID 440326 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].C1CCN2C(=NCCC2)CC1.[OH:20][CH:21]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[CH:22]1[CH2:24][CH2:23]1>C1COCC1>[O:20]([CH:21]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[CH:22]1[CH2:24][CH2:23]1)[Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 224069731211507-79-7

Product 1

HCID 53920845HCID 53920845, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBDMSCl (3.5 g, 23.2 mmol) and DBU (3.5 mL, 23.2 mmol) were added to a solution of 2-(1-hydroxy-1-cyclopropylmethyl)thiazole (3.0 g, 19.4 mmol) in dry THF (40 mL). The mixture was stirred at rt for 16 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 using 5% EtOAc/hexane to give 4.97 g (95%) of 2-(1-t-butyldimethylsiloxy-1-cyclopropylmethyl)thiazole as a colorless 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-5987a7b55de444e6a596bfe07c062b49
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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