Triethylamine → 2-(1,3-dihydro-2H-isoindol-2-yl)ethanol

HRID 1762471Notes

Reaction equation

HRID 1762471 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.Br[CH2:11][CH2:12][OH:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[OH:13][CH2:12][CH2:11][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 422478Isoindoline

Product 1

HCID 122503792-(1,3-dihydro-2H-isoindol-2-yl)ethanolYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.85 g (0.0252 mol) of isoindoline, 2.99 g (0.0252 mol) of 2-bromoethanol and 5.09 g (0.05 mol) of triethylamine in 100 ml of dry toluene was refluxed for 12 hours. After cooling the mixture was filtered, concentrated in vacuo, dissolved in ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate and concentrated in vacuo to yield 2.58 g (63%) of a dark red oil. NMR (CDCl3) δ 2.78 (2H, t), 3.52 (2H, t), 3.82 (4H, s), 7.0 (4H, s)

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3628b7f15ce74ec9bdb1256b4f8391ab
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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