Hydrochloric Acid → HCID 59637736, compound

HRID 1892017Notes

Reaction equation

HRID 1892017 reaction equation
C([OH:4])C#C.[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12].Cl.N1C=C[CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:12][CH2:16][C:17]#[CH:18])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7859Propargyl alcohol2×HCID 898486-Bromohexanoyl chloride

Product 1

HCID 59637736HCID 59637736, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Propargyl alcohol (0.5 mL, 3.41 mmol, 1 eq.) was dissolved in 10 mL of dry pyridine and 10 mL of dry benzene under argon and this solution was cooled in an ice bath. 6-bromohexanoyl chloride (0.612 mL, 4.1 mmol, 1.2 eq.) dissolved in 10 mL of dry benzene under argon was then added dropwise to the propargyl alcohol solution and stirred overnight. The solution was acidified with 1M HCl, then extracted twice with CH2Cl2. The organic layers were twice washed with 1M NaOH, once washed with brine, and dried over Na2SO4. The solvent was removed on a rotary evaporator to yield a light brown oil.

Workup

  1. extractionextracted twice with CH2Cl2
  2. washThe organic layers were twice washed with 1M NaOH
  3. washonce washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed on a rotary evaporator
  6. customto yield a light brown oil

Sources & evidence

ORD record
ord-64deded968c14208b508c33660135e30
Source dataset
uspto-grants-2013_08
Patent number
US08507572B2

Reaction notes

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