Water → HCID 67546464, compound

HRID 2251837Notes

Reaction equation

HRID 2251837 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].[H-].[Na+].[CH3:17]I.O>C1COCC1>[CH3:17][O:4][CH2:3][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:1])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 222492792-Methyl-2-(4-nitrophenyl)propan-1-ol

Product 1

HCID 67546464HCID 67546464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-methyl-2-(4-nitro-phenyl)-propan-1-ol (prepared by the method described in WO02/66470) (200 mg, 1 mmol) in THF (15 mL) was added NaH (43 mg, 60% in oil) at 0° C. The mixture was stirred at 0° C. for 20 min, MeI (0.22 mL, 1.5 mmol) was added and the mixture was stirred for 2 h at 0° C. then overnight at RT. H2O was added and the mixture was extracted with EtOAc. The organic phase was dried, filtered and evaporated to give 1-(2-methoxy-1,1-dimethyl-ethyl)-4-nitro-benzene.

Workup

  1. stirringthe mixture was stirred for 2 h at 0° C.
  2. customovernight
  3. customat RT
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7a35f7e0a3f247b2a64f8c7aab5c0a0c
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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