Water → HCID 67081893, compound

HRID 1666305Notes

Reaction equation

HRID 1666305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH:6]=[N:7][NH:8]C(OC(C)(C)C)=O.[OH-].[Na+].O.[C:22]([O:25]CC)(=[O:24])C.[C:28]1([CH3:34])[CH:33]=CC=C[CH:29]=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][N:7]([NH2:8])[C:22]([O:25][C:28]([CH3:34])([CH3:33])[CH3:29])=[O:24]

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2692519HCID 2692519, compound

Product 1

HCID 67081893HCID 67081893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium dihydrido-bis(2-methoxy-ethoxy)aluminate (66 ml of a 3.5 M solution in toluene) in tetrahydrofuran (15 ml) was added to t-butyl 3-methoxy-benzylidenecarbazate (28.8 g) dissolved in tetrahydrofuran (200 ml) at 20° C. during 45 minutes. After the addition the solution was stirred at room temperature for 3 hours. The reaction mixture was treated carefully with aqueous sodium hydroxide (40 ml, 5%), after which water (200 ml) and ethyl acetate (500 ml) were added. The organic phase was separated, dried and concentrated to dryness giving t-butyl 3-methoxy-benzylcarbazate (28 g) as an oil.

Workup

  1. additionAfter the addition the solution
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9eec602d81ae408da76eb7d718fc0d96
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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