Imidazole → (6-Bromo-thiochroman-4-yl-oxy)-tert-butyl-dimethyl-silane

HRID 1174693Notes

Reaction equation

HRID 1174693 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2=[O:12].[BH4-].[Na+].BrC1C=C2C(=CC=1)SCCC2O.N1C=CN=C1.[CH3:32][C:33]([Si:36](Cl)([CH3:38])[CH3:37])([CH3:35])[CH3:34]>CO.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][CH:5]2[O:12][Si:36]([C:33]([CH3:35])([CH3:34])[CH3:32])([CH3:38])[CH3:37]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 4311764Sodium borohydrideHCID 139537366-Bromo-2,3-dihydro-4H-1-benzothiopyran-4-oneHCID 177966436-Bromo-thiochroman-4-ol

Product 1

HCID 59749549(6-Bromo-thiochroman-4-yl-oxy)-tert-butyl-dimethyl-silane

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

6-Bromo-thiochroman-4-one (Intermediate-K2) (prepared according to the procedures found in Johnson, A. T. et al Bioorg Med. Chem. 1999, 7, 1321. incorporated herein by reference) (1.11 g, 4.6 mmol) in MeOH (46 mL) was treated with sodium borohydride (0.14 g, 4.6 mmol) at 0° C. for 30 m. The mixture was subjected to a standard aqueous work-up and the alcohol, 6-bromo-thiochroman-4-ol, was used in the next step without further purification. 6-Bromo-thiochroman-4-ol (˜4.5 mmol) in DMF (20 mL) was treated with imidazole (0.31 g) and TBSCl (0.69 g) at rt for 16 h. After an aqueous work-up the residue was purified by chromatography on silica gel with 10% EtOAc: hexanes to afford (6-bromo-thiochroman-4-yl-oxy)-tert-butyl-dimethyl-silane (Intermediate-K3) as a yellow oil, 1.06 g.

Workup

  1. customthe alcohol, 6-bromo-thiochroman-4-ol, was used in the next step without further purification
  2. customAfter an aqueous work-up the residue was purified by chromatography on silica gel with 10% EtOAc

Sources & evidence

ORD record
ord-776a250d4a6b46d3837697c1ffc4bdb5
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

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