Imidazole → 4,4-Dimethyl-7-[(t-butyldimethylsilyl)oxy]-1-tetralone

HRID 265429Notes

Reaction equation

HRID 265429 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[C:5](=[O:13])[CH2:4][CH2:3]1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([O:12][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:9][CH:10]=2)[C:5](=[O:13])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 221018653,4-Dihydro-7-hydroxy-4,4-dimethyl-1(2H)-naphthalenone

Product 1

HCID 190344734,4-Dimethyl-7-[(t-butyldimethylsilyl)oxy]-1-tetralone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound XIV (2.00 g, 10.5 mmol) in dimethylformamide (16 mL) was added tert-butyldimethylsilyl chloride (1.90 g, 12.6 mmol) and imidazole (1.79 g, 26.3 mmol) at room temperature. After 5 hours, 5% NaHCO3 (50 mL) was added and the mixture was extracted with hexane (2×75 mL). The combined organic phases were dried over anhydrous magnesium sulfate and concentrated in vacuo to give 3.22 g (Y: 99%) of the title compound; 1H-NMR (CDCl3): δ 7.44 (d, J=2.8 Hz, 1H), 7.29 (d, J=8.7 Hz, 1H), 7.01 (dd, J=8.7, 2.8 Hz, 1H), 2.71 (t, J=7.0 Hz, 2H), 1.99 (t, J=7.0 Hz, 2H), 1.36 (s, 6H), 0.98 (s, 9H), 0.20 (s, 6H); MS (DCI) m/e: 305 (MH+).

Workup

  1. extractionthe mixture was extracted with hexane (2×75 mL)
  2. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe94fa0de3714695a8716f8148edaac4
Source dataset
uspto-grants-1997_07
Patent number
US05648385

Reaction notes

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