Propargyl bromide → HCID 131717796, compound

HRID 258026Notes

Reaction equation

HRID 258026 reaction equation
[OH:1][C:2]1[C:10]2[O:9][CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.CO[C:17]1[C:25]2OC(C(O)=O)CC=2C=C[CH:18]=1.O[C:30]1C=CC=C2C=1C=C1C(=C2)C(=O)CCC1.C(Br)C#C.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[CH2:25]([O:1][C:2]1[C:10]2[O:9][CH:8]([C:11]([O:13][CH2:14][CH3:30])=[O:12])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:17]#[CH:18]

Participants

7

Reactant 5

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 13164957HCID 13164957, compoundHCID 19782186HCID 19782186, compoundHCID 19782200HCID 19782200, compound

Product 1

HCID 131717796HCID 131717796, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

37.57 g (0.194 mol) of methyl 7-hydroxy-2,3-dihydro-benzofuran-2-carboxylate [prepared from the known 7-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid, G. Goldenberg et al., Chim. Ther. 8 (3), 1973, 259-270] and 32.85 g (0.213 mol) of propargyl bromide (80% in toluene) are refluxed in the presence of 29.49 g (0.213 mol) of K2CO3 in 194 ml of dry butanone for 5 h. After cooling, the precipitate is filtered off and washed well with acetone, and the filtrate is evaporated. The residue is taken up in 200 ml of CH2Cl2, shaken twice with 10% strength NaOH solution, dried over Na2SO4 and evaporated. The residue is flash chromatographed on silica gel (eluent: petroleum ether/acetone 5:1).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off
  3. washwashed well with acetone
  4. customthe filtrate is evaporated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customchromatographed on silica gel (eluent: petroleum ether/acetone 5:1)

Sources & evidence

ORD record
ord-3835d4c23325471e93541b3638f40044
Source dataset
uspto-grants-1993_11
Patent number
US05264458

Reaction notes

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