Hydrochloric Acid → HCID 68536320, compound

HRID 1992831Notes

Reaction equation

HRID 1992831 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:28]=[CH:29]/[C:30]([O:32]CC)=[O:31])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH3:21])[C:10]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+].Cl>CCO.C1COCC1>[F:1][C:2]1[CH:3]=[C:4](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH3:21])[C:10]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86616641HCID 86616641, compound

Product 1

HCID 68536320HCID 68536320, compoundYield 164.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 25 (130 mg, 0.29 mmol, 1 equiv) was dissolved in EtOH (5 mL) and THF (5 mL). A solution of 1 N NaOH (2.9 mL, 2.85 mmol, 10 equiv)) was added and the solution refluxed for 1.5 h. The reaction was cooled to RT and then acidified to pH 2 with 1 N HCl. The product was extracted with EtOAc (100 mL) and the organic layer was washed with saturated aqueous NaCl (50 mL), dried over Na2SO4, filtered and concentrated to provide the title compound (26) (204 mg, 100%), as a pale yellow solid. 1HNMR (400 MHz, DMSO-d6): δ 7.74 (s, 1H), 7.58 (m, 2), 7.38 (m, 2H), 7.32-7.16 (m, 6H), 7.11 (m, 1H), 6.36 (m, 2H), 3.87 (s, 3H), 2.18 (s, 3H). LRMS m/z 429.4 (M+H)+.

Workup

  1. temperaturethe solution refluxed for 1.5 h
  2. extractionThe product was extracted with EtOAc (100 mL)
  3. washthe organic layer was washed with saturated aqueous NaCl (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-000fd834461b42ed85f7c0b48db16d26
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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