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

HRID 747285Notes

Reaction equation

HRID 747285 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-e3c830f1be654d9aaa54c1197cf01595
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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