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

HRID 647317Notes

Reaction equation

HRID 647317 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-80a197316dfe42e8b6172d27a1722bcd
Source dataset
uspto-grants-1983_10
Patent number
US04408057

Reaction notes

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