tert-Butyldimethylsilyl chloride → HCID 22607178, compound

HRID 2307804Notes

Reaction equation

HRID 2307804 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[CH3:9][C:10]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])[CH3:11].C([O-])(O)=O.[Na+]>>[C:10]([Si:13]([CH3:15])([CH3:14])[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1)([CH3:12])([CH3:11])[CH3:9]

Participants

4

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 27631086-Fluoropyridin-3-ol

Product 1

HCID 22607178HCID 22607178, compoundYield 98%

Procedure

A mixture of 2-fluoro-5-hydroxypyridine (1.00 g, 8.84 mmol) and BDCS reagent (0.5 TBSCl, 1.0 imidazole in DMF) (35.4 mL, 17.7 mmol) was stirred at rt for 1 h. The reaction was poured into satd. aqueous NaHCO3 solution. The aqueous layer was extracted with ether. The combined extracts were washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 10% ethyl acetate/hexanes to give the title compound (1.96 g, 98%).

Workup

  1. additionThe reaction was poured into satd
  2. extractionThe aqueous layer was extracted with ether
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-83f7293b1bc94bbca46c7dcdb7063089
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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