Hydrochloric Acid → HCID 13685267, compound

HRID 369547Notes

Reaction equation

HRID 369547 reaction equation
O.[OH-].[Li+].[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15](C2C=CC=CC=2C([O-])=O)=[CH:14][C:13]=1[N+:27]([O-:29])=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1C[O:33]CC1.Cl>CO.O>[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:33])=[CH:14][C:13]=1[N+:27]([O-:29])=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86755962HCID 86755962, compound

Product 1

HCID 13685267HCID 13685267, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (5.632 g, 134.2 mmol) was added to a stirred solution of compound 53 (2.343 g, 6.71 mmol) in 150 ml methanol and 50 ml water. THF (50 ml) was added after 20 minutes to increase solubility. The reaction mixture was stirred overnight and was then acidified with concentrated HCl. The reaction mixture was extracted five times with dichloromethane, and the combined organic layers were washed with brine and dried over MgSO4. The crude product was purified via flash chromatography over silica gel with gradual elutions from 80/10-50/50 (Hex/EtOAc). Evaporation of solvent yielded 1.567 g (95%) of a yellow solid.

Workup

  1. temperatureto increase solubility
  2. extractionThe reaction mixture was extracted five times with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified via flash chromatography over silica gel with gradual elutions from 80/10-50/50 (Hex/EtOAc)
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-b11a7f5f38414c84939fbadadfd66a9d
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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