Hydrochloric Acid → HCID 59527303, compound

HRID 384478Notes

Reaction equation

HRID 384478 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6]Br.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26]CC)=O)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>C1COCC1>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]2([OH:26])[CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:20][CH:21]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 563839Ethyl 3-[4-(benzyloxy)phenyl]propanoateHCID 5462224Magnesium

Product 1

HCID 59527303HCID 59527303, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of magnesium (120 mg) and THF (1.5 mL) was added 1,4-dibromobutane (0.2 mL) at room temperature under nitrogen flow, followed by stirring for 1 hour. The reaction solution was ice-cooled, and a solution of ethyl 3-[4-(benzyloxy)phenyl]propanoate (400 mg) in THF (3 mL) was added dropwise thereto while maintaining an internal temperature of 10° C. or less. The reaction mixture was stirred under ice-cooling for 3 hours, and allowed to stand overnight at room temperature. The reaction liquid was ice-cooled and was adjusted to an acidic pH by adding 1M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/3-1/1) to obtain 1-{2-[4-(benzyloxy)phenyl]ethyl}cyclopentanol (145 mg).

Workup

  1. temperaturecooled
  2. temperaturewhile maintaining an internal temperature of 10° C. or less
  3. stirringThe reaction mixture was stirred under ice-
  4. temperaturecooling for 3 hours
  5. waitto stand overnight at room temperature
  6. customThe reaction liquid
  7. temperaturecooled
  8. extractionfollowed by extraction with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/3-1/1)

Sources & evidence

ORD record
ord-aa776466770d462f943f97bc055391d0
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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