Hydrochloric Acid → HCID 68731668, compound

HRID 884073Notes

Reaction equation

HRID 884073 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7](/[C:11](=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:18][CH3:19])/[C:12]([O:14]CC)=[O:13])[CH:8]=[CH:9][CH:10]=1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7](/[C:11](=[C:17](\[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)/[CH2:18][CH3:19])/[C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86630295HCID 86630295, compound

Product 1

HCID 68731668HCID 68731668, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2a (195 mg, 0.573 mmol) in MeOH (6 ml) was added 2N NaOH (3 ml) and the mixture was stirred at 80° C. for 15 h. After cooling, 2 N HCl (3 ml) was added drop wise under ice cooling, and the whole was extracted with AcOEt, the organic layer was washed with brine, dried over Na2SO4, then concentrated. The residual solid was triturated with hexanes to give 3a (69%). 3a: colorless powder; 1H-NMR (CDCl3) δ 1.04 (3H, t, J=7.5 Hz), 2.83 (2H, t, J=7.5 Hz), 3.34 (3H, s), 4.93 (2H, s), 6.68 (1H, m), 6.73 (1H, d, J=7.6 Hz), 6.77 (2H, dd, J=2.5, 7.8 Hz), 7.01-7.07 (3H, m), 7.10-7.18 (3H, m).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with AcOEt
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residual solid was triturated with hexanes

Sources & evidence

ORD record
ord-fb5e58e7977a4a24b21c9f02ec57e9ad
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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