Toluene → HCID 59439469, compound

HRID 1640071Notes

Reaction equation

HRID 1640071 reaction equation
[CH:1]([N-:4][CH:5]([CH3:7])C)([CH3:3])C.[Li+].[O:9]1CCC[CH2:10]1.C(N(CC)C([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:21]=1[CH3:28])=O)C.C1(C)C=CC=CC=1>O>[CH2:5]([N:4]([CH2:1][CH3:3])[C:10](=[O:9])[CH2:28][C:21]1[C:22]([O:26][CH3:27])=[CH:23][CH:24]=[CH:25][C:20]=1[OH:19])[CH3:7]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 594394762-(N,N-diethylcarbamoyloxy)-6-methoxytoluene

Product 1

HCID 59439469HCID 59439469, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 mL of lithium diisopropylamide (2M/tetrahydrofuran-ethylbenzene, 10 mmol) was stirred and cooled on dry ice-ethanol bath and 8.0 mL tetrahydrofuran solution containing 0.95 g (4.0 mmol) of 2-(N,N-diethylcarbamoyloxy)-6-methoxytoluene was added dropwise thereto over 16 minutes. After one minute, warming was started under room temperature and after the mixture was stirred for 47 minutes, it was allowed to stand overnight. 10 mL of toluene and 10 mL of water were added thereto and after the mixture was stirred for 4 minutes, it was transferred into a separatory funnel and settled. The aqueous layer was separated and collected and combined with aqueous layers extracted from the organic layer with 2 N potassium hydroxide aqueous solution twice (5.0 mL for each time). After this aqueous layer was washed with 10 mL of toluene, 10 mL of toluene was added therein and 20 mL of 2 N hydrochloric acid aqueous solution was added thereto while being stirred and the mixture was transferred into a separatory funnel and settled. The organic layer was separated and collected and combined with the organic layer extracted from the aqueous layer with 5 mL of toluene. This organic layer was washed with 5 mL of water twice and then concentrated in vacuo, and thereby 0.81 g of the title compound was obtained.

Workup

  1. temperaturecooled on dry ice-ethanol bath
  2. additionwas added dropwise
  3. waitAfter one minute
  4. temperaturewarming
  5. customwas started under room temperature
  6. waitto stand overnight
  7. stirringafter the mixture was stirred for 4 minutes
  8. customit was transferred into a separatory funnel
  9. customThe aqueous layer was separated
  10. customcollected
  11. extractionextracted from the organic layer with 2 N potassium hydroxide aqueous solution twice (5.0 mL for each time)
  12. washAfter this aqueous layer was washed with 10 mL of toluene, 10 mL of toluene
  13. additionwas added
  14. addition20 mL of 2 N hydrochloric acid aqueous solution was added
  15. stirringwhile being stirred
  16. customthe mixture was transferred into a separatory funnel
  17. customThe organic layer was separated
  18. customcollected
  19. extractionextracted from the aqueous layer with 5 mL of toluene
  20. washThis organic layer was washed with 5 mL of water twice
  21. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c990343181af4bfaa4147ef14cfa493e
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

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