Water → HCID 58001774, compound

HRID 420741Notes

Reaction equation

HRID 420741 reaction equation
[Cl:1][C:2]1[C:3](C(OC)=O)=[N:4][CH:5]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:7]=1.[CH3:21][Mg]Br.[NH4+].[Cl-].O.CCO[C:30]([CH3:32])=[O:31]>C1COCC1>[Cl:1][C:2]1[C:3]([C:30]([OH:31])([CH3:32])[CH3:21])=[N:4][CH:5]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12])[CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 58001760HCID 58001760, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58001774HCID 58001774, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-chloro-5-({[(1,1 dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-pyridinecarboxylate (488 mg, 1.545 mmol) in THF (5 ml) at −23° C. was added methylmagnesium bromide (4.12 ml, 12.36 mmol) dropwise. After addition, the solution was allowed to warm to rt and stirred for 5 h. Saturated NH4Cl was added after cooling the solution to 0° C. Water and EtOAc were added and the aqueous phase was extracted with EtOAc. The solution was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by Flashmaster chromatography on a 10 g silica gel cartridge using hexane/EtOAc 95:5 as eluent to obtain 2-[3-chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-pyridinyl]-2-propanol (328 mg, 60% yield) as colourless oil.

Workup

  1. additionAfter addition
  2. temperatureafter cooling the solution to 0° C
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by Flashmaster chromatography on a 10 g silica gel cartridge

Sources & evidence

ORD record
ord-c626a3e6682d4b9bb90c87a0b008f561
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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