Iodoethane → HCID 67776885, compound

HRID 2065788Notes

Reaction equation

HRID 2065788 reaction equation
[OH:1][CH2:2][C@@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4].I[CH2:17][CH3:18].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[CH2:17]([O:1][CH2:2][C@@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4])[CH3:18]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 124997532-[(1S)-2-Hydroxy-1-methylethyl]-1H-isoindole-1,3(2H)-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 67776885HCID 67776885, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(1S)-2-hydroxy-1-methyl-ethyl]isoindoline-1,3-dione (47 g, 229 mmol) and iodoethane (89.3 g, 572.5 mmol) in THF (376 mL) is added potassium tert-butoxide (64.25 g, 572.5 mmol) in one portion. The mixture is stirred under a nitrogen atmosphere for 15 h. The mixture is diluted with ethyl acetate (200 mL) and washed with brine (200 mL). The aqueous phase is extracted with ethyl acetate (2×100 mL). The combined organic extracts are dried over MgSO4, filtered, concentrated under reduced pressure, and then dried under high vacuum to afford the title compound (39.4 g, 74%) as an orange solid that is used without further purification. LC-ES/MS m/z 234 (M+1).

Workup

  1. washwashed with brine (200 mL)
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-4216711a80fe47c28c6b517d00b24149
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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