Water → HCID 11001770, compound

HRID 1358557Notes

Reaction equation

HRID 1358557 reaction equation
Br[CH:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[Cl:16])[C:9](=[O:17])[C:8]2[C:7]([Cl:18])=[CH:6][CH:5]=[CH:4][C:3]1=2.C(=O)([O-])[O-].[Ca+2].[CH2:24]([OH:27])[CH2:25][CH3:26].O>C1COCC1>[CH2:24]([O:27][CH:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[Cl:16])[C:9](=[O:17])[C:8]2[C:7]([Cl:18])=[CH:6][CH:5]=[CH:4][C:3]1=2)[CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 10311-PropanolHCID 10112Calcium CarbonateHCID 12082572HCID 12082572, compound

Product 1

HCID 11001770HCID 11001770, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound (6) (2.0 mmol) and anhydrous calcium carbonate (0.5 g) in dry THF (20 ml) was added dropwise a solution of an appropriate propanol (10 ml) in dry THF (10 ml) under N2. The reaction mixture was refluxed for 3 hours. Water (250 ml) was added and then extracted with dichloromethane. The combined organic extracts were washed with water, dried (MgSO4), and concentrated. The resulting precipitate was collected by filtration, washed with water and further purified by crystallization (CH3CN).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customfurther purified by crystallization (CH3CN)

Sources & evidence

ORD record
ord-0ec6c36c24ce4f149a504f6facaa2d6a
Source dataset
uspto-grants-2003_07
Patent number
US06596774B1

Reaction notes

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