Dihydrobenzofuran → HCID 12379536, compound

HRID 626222Notes

Reaction equation

HRID 626222 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][C:8](Cl)=[O:9].[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12]1>C(Cl)Cl>[Cl:5][CH2:6][CH2:7][C:8]([C:18]1[CH:17]=[CH:16][C:15]2[O:11][CH2:12][CH2:13][C:14]=2[CH:19]=1)=[O:9]

Participants

5

Reactant 3

HCID 10329DihydrobenzofuranHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12379536HCID 12379536, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of AlCl3 (2.22 g, 1.0 eq) in 50 mL CH2Cl2 was added 3-chloropropanoyl chloride (2.54 g, 1.2 eq) dropwise. The mixture was stirred at rt for 10 min, then 2,3-dihydrobenzofuran (2.0 g, 1.0 eq) was added. After stirring at rt overnight, the mixture was quenched with cold water and then extracted with CH2Cl2. The extract was dried over Na2SO4, filtered, the filtrate was concentrated and purified by column chromatography on silica gel to give the desired product (1.5 g, 62%). 1H NMR (400 MHz, CDCl3) δ 7.86 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 4.68 (t, J=8.8 Hz, 2H), 3.92 (t, J=6.8 Hz, 2H), 3.40 (t, J=8.8 Hz, 2H), 3.26 (t, J=6.8 Hz, 2H).

Workup

  1. stirringAfter stirring at rt overnight
  2. customthe mixture was quenched with cold water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe extract was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a63f552483dc4705bad1094b651acd5a
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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