Hydrochloric Acid → HCID 22485789, compound

HRID 2181265Notes

Reaction equation

HRID 2181265 reaction equation
[C:1]([Si:5]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[O:6][C:7]1[CH:8]=[C:9]([C:13]2(O)[CH:25]([CH2:26][N:27]([CH3:29])[CH3:28])[CH2:24][CH2:23][C:15]3(OCC(C)(C)C[O:16]3)[CH2:14]2)[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([Si:5]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:25]([CH2:26][N:27]([CH3:29])[CH3:28])[CH2:24][CH2:23][C:15](=[O:16])[CH:14]=2)[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22485793HCID 22485793, compound

Product 1

HCID 22485789HCID 22485789, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

197 g 8-[3-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-9-dimethylaminomethyl-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-8-ol were dissolved in tetrahydrofuran and the solution was cooled to 5° C. A mixture of 300 ml concentrated hydrochloric acid and 300 ml water was added dropwise at this temperature. The mixture was then stirred at room temperature for 10 hours. 400 ml ethyl acetate were then added, while cooling with ice, and the pH was then brought to 12 with 32% sodium hydroxide solution. The phases were separated and the aqueous phase was extracted three times with 400 ml ethyl acetate each time. The combined organic phases were washed twice with 100 ml saturated sodium chloride solution each time and dried over magnesium sulfate and the solvent was then evaporated in vacuo. The residue was purified on silica gel with ethyl acetate/methanol=1/1. 68 g (42% of theory) of the title compound were obtained in this way.

Workup

  1. additionwas added dropwise at this temperature
  2. temperaturewhile cooling with ice
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted three times with 400 ml ethyl acetate each time
  5. washThe combined organic phases were washed twice with 100 ml saturated sodium chloride solution each time
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was then evaporated in vacuo
  8. customThe residue was purified on silica gel with ethyl acetate/methanol=1/1

Sources & evidence

ORD record
ord-61032ea0fb384f409b1f391cb3edb64d
Source dataset
uspto-grants-2005_05
Patent number
US06890959B2

Reaction notes

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