Hydrochloric Acid → HCID 18000984, compound

HRID 478312Notes

Reaction equation

HRID 478312 reaction equation
[H-].[Na+].[C:3]([C:5]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6]1)#[CH:4].Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].Cl>O1CCCC1.C(OCC)(=O)C>[CH3:16][O:15][C:13](=[O:14])[CH2:12][O:10][C:5]1([C:3]#[CH:4])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 870741-Ethynylcyclopentanol

Product 1

HCID 18000984HCID 18000984, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mechanically stirred suspension of sodium hydride (60% dispersion in mineral oil, 1.5 g, 38 mmol) in tetrahydrofuran (10 mL) at 0 C. under nitrogen was treated with a solution of 1-ethynylcyclopentanol (5.0 g, 45 mmol) in tetrahydrofuran (20 mL) over 15 minutes. After stirring at 0 C. for 1 hour, the mixture was treated with methyl bromoacetate (5.4 mL, 56 mmol). after stirring at ambient temperature for 16 hours, the mixture was treated with 2M HCl (25 mL) and then treated with ethyl acetate (25 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered, concentrated and used without purification in the next step.

Workup

  1. stirringafter stirring at ambient temperature for 16 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customused without purification in the next step

Sources & evidence

ORD record
ord-a8c288545e274727a99e384dbfd06572
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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