3-Isopropyl-4-methoxybenzaldehyde → HCID 22662124, compound

HRID 392886

Reaction equation

HRID 392886 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:17].C[Li].C([Li])(C)(C)C.[CH:25]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH:31]=[O:32])([CH3:27])[CH3:26]>C1CCCCC1.CCOCC.CCCCC.CCOCC.C1CCCCC1.O>[OH:32][CH:31]([C:30]1[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:28]([CH:25]([CH3:27])[CH3:26])[CH:29]=1)[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:17]

Participants

10

Reactant 4

HCID 98989903-Isopropyl-4-methoxybenzaldehydeHCID 22662122tert-Butyl (4-bromo-3,5-dimethylphenyl)carbamateHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22662124HCID 22662124, compoundYield 65.6%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 8003PentaneSolventHCID 8078CyclohexaneSolventHCID 21895417Cyclohexane diethyletherSolvent

Procedure

970 mg (3.23 mmol) of tert-butyl 4-bromo-3,5-dimethylphenylcarbamate (Example IV) are dissolved in 3 ml of cyclohexane and 3 ml of ether, cooled to −78° C., and added dropwise to 2.53 ml of 1.6 M methyllithium in ether at −78° C. After stirring at this temperature for 10 minutes, 3.8 ml of 1.7 M tert-butyllithium in pentane are added dropwise. The mixture is stirred at −78° C. for 1 hour and, after addition of 518 mg (2.9 mmol) of 3-isopropyl-4-methoxybenzaldehyde dissolved in 1 ml of ether/cyclohexane (1/1), stirred at −78° C. for 30 min and at room temperature for one hour. It is diluted with water and ether, the organic phase is washed with 10% strength citric acid solution, sodium bicarbonate solution and water and dried over sodium sulphate, and the solvent is removed in vacuo. Purification by chromatography (cyclohexane/ethyl acetate=9:1) affords 0.76 g (53%) of tert-butyl 4-[hydroxy(4-methoxy-3-isopropylphenyl)methyl]-3,5-dimethylphenylcarbamate.

Workup

  1. stirringThe mixture is stirred at −78° C. for 1 hour
  2. stirringstirred at −78° C. for 30 min and at room temperature for one hour
  3. washthe organic phase is washed with 10% strength citric acid solution, sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is removed in vacuo
  6. customPurification by chromatography (cyclohexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-39b626e8ea814c1fb5335a2e62d1f4d6
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Linked notes

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