Triethylamine → (4-Bromo-5-isopropyl-thiophen-2-yl-methoxy)-tert-butyl-dimethyl-silane

HRID 1859538Notes

Reaction equation

HRID 1859538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[S:5][C:6]=1[CH:7]([CH3:9])[CH3:8].CCN(CC)CC.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][O:11][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[S:5][C:6]=1[CH:7]([CH3:9])[CH3:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 22572878(4-Bromo-5-isopropyl-thiophen-2-yl)-methanol

Product 1

HCID 22572987(4-Bromo-5-isopropyl-thiophen-2-yl-methoxy)-tert-butyl-dimethyl-silane

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (4-bromo-5-isopropyl-thiophen-2-yl)-methanol (Example Q; 3.4 g, 14 mmol) in CH2Cl2 (4.0 mL) was treated with NEt3 (2.8 mL, 20 mmol), p-dimethylaminopyridine (0.050 g), and t-butyldimethylsilylchloride (2.41 g, 16.0 mmol). The mixture was stirred for 14 hours, then diluted with Et2O and washed with H2O. The organic layer was dried (MgSO4) and the solvent evaporated to provide the crude product, which was used without further purification.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-def7206ba8d44b9bb5b518a55d83c7d8
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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