Sodium Bicarbonate → HCID 58056190, compound

HRID 1773491Notes

Reaction equation

HRID 1773491 reaction equation
[C:1]([Si:5]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[N+:23]([O-])=O)[CH2:11][CH2:10]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+]>C(O)C.CCCCCC>[C:1]([Si:5]([CH3:7])([CH3:6])[O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[NH2:23])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[O:15][CH:12]1[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH2:11]1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 58056154HCID 58056154, compound

Product 2

HCID 58056190HCID 58056190, compoundYield 42%HCID 58056330HCID 58056330, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

Stannous chloride (3.2 g, 16.98 mmol) was added to a solution of tert-butyl-[4-(4-chloro-2-nitro-phenoxy)-cyclohexyloxy]-dimethyl-silane (1.28 g, 3.32 mmol) in a mixture of ethanol and ethyl acetate (1/1, 40 mL) and the resulting mixture was stirred at room temperature for 24 hours. Ice and an aqueous solution of sodium bicarbonate (5%, 150 mL) were added and the solid formed was filtered, washed with ethyl acetate and discarded. The layers of the filtrate were separated and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered through a CELITE™ pad and evaporated under reduced pressure. The yellow oily residue was purified by flash chromatography (EtOAc/hexane, from 5/95 to 80/20) to give 0.5 g (42% yield) of 2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-phenylamine as a yellow oil and 803 mg (16% yield) of 4-(2-amino-4-chloro-phenoxy)-cyclohexanol.

Workup

  1. customthe solid formed
  2. filtrationwas filtered
  3. washwashed with ethyl acetate
  4. customThe layers of the filtrate were separated
  5. extractionthe aqueous layer was extracted 3 times with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered through a CELITE™ pad
  9. customevaporated under reduced pressure
  10. customThe yellow oily residue was purified by flash chromatography (EtOAc/hexane, from 5/95 to 80/20)

Sources & evidence

ORD record
ord-b1aadcfe42b4437582187e2389c4a551
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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