Hydrochloric Acid → HCID 22266846, compound

HRID 1875482Notes

Reaction equation

HRID 1875482 reaction equation
[C:1]([C:4](C)([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C)C)[C:5](OCC)=O)(=[O:3])[CH3:2].[OH-].[Na+].Cl>CO.O>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:4]([CH3:5])[C:1](=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58165753HCID 58165753, compound

Product 1

HCID 22266846HCID 22266846, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-acetyl-8-(tert-butyldimethylsilyloxy)-2-methyloctanoate (13.5 g, 37.65 mmol) was dissolved in 10 mL CH3OH to which 5 g NaOH in 50 mL water was then added. The mixture was then heated to 50° C. overnight. The volume of the reaction mixture was reduced to about 50 mL under reduced pressure and acidified to pH 1 by the addition of 2 M HCl. This resulting mixture was heated to 60° C. for 5 hours. After cooling to room temperature the product was extracted into EtOAc. Concentration gave a yellow oil that was subjected to silica gel chromatography affording a colorless oil (4.25 g, 65.5%). 1H-NMR (300 MHz, CDCl3): δ 3.60 (t, 2H) 2.46 (m, 1H), 2.09 (s, 3H), 1.54 (m, 4H), 1.30 (m, 6H), 1.04 (d, 3H) ppm; MS m/z calculated for C10H20O2 (M+H): 173.2. Found 173.1 (M+H, ESI+).

Workup

  1. additionwas then added
  2. temperatureThis resulting mixture was heated to 60° C. for 5 hours
  3. temperatureAfter cooling to room temperature the product
  4. extractionwas extracted into EtOAc
  5. concentrationConcentration
  6. customgave a yellow oil that

Sources & evidence

ORD record
ord-064edbd88ee54e069344bb1e9a007c95
Source dataset
uspto-grants-2012_11
Patent number
US08309059B2

Reaction notes

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