Sodium Chloride → 4-(1-Pyrrolyl)-2-indanyl acetate

HRID 325780

Reaction equation

HRID 325780 reaction equation
[C:1]([O:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:14])[CH2:6]1)(=[O:3])[CH3:2].CO[CH:17]1[CH2:21][CH2:20][CH:19](OC)O1.C(Cl)(Cl)Cl.[Cl-].[Na+]>C(O)(=O)C>[C:1]([O:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:14]2[CH:17]=[CH:21][CH:20]=[CH:19]2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6212ChloroformHCID 790982,5-DimethoxytetrahydrofuranHCID 132395844-amino-2,3-dihydro-1H-inden-2-yl acetate

Product 1

HCID 132395854-(1-Pyrrolyl)-2-indanyl acetateYield 92.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 0.70 g (0.004 mole) of 4-amino-2-indanyl acetate and 0.56 g (0.004 mole) of 2,5-dimethoxytetrahydrofuran in 1.5 mL of acetic acid was heated under reflux for 3 hours. The reaction mixture was cooled to ambient temperature and poured into 30 mL of chloroform. The mixture was stirred with 30 mL of an aqueous saturated solution of sodium chloride. The organic layer was removed, and the aqueous layer extracted with two portions of 30 mL each of chloroform. The combined organic phases were washed with two portions of 30 mL each of an aqueous saturated solution of sodium chloride. The organic layer was dried over potassium carbonate, filtered, and the filtrate concentrated under reduced pressure to give 0.89 g of 4-(1-pyrrolyl)-2-indanyl acetate.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe organic layer was removed
  3. extractionthe aqueous layer extracted with two portions of 30 mL each of chloroform
  4. washThe combined organic phases were washed with two portions of 30 mL each of an aqueous saturated solution of sodium chloride
  5. dry with materialThe organic layer was dried over potassium carbonate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-6026cbe3961349f19be75300a73f0442
Source dataset
uspto-grants-1984_04
Patent number
US04442296

Linked notes

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