Acetic Acid → HCID 10132157, compound

HRID 1357877Notes

Reaction equation

HRID 1357877 reaction equation
C(O)(=O)C.C([Si](C)(C)[O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH2:17][C:18]2(O)[C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)=[CH:13][C:12]=1[O:34][CH3:35])(C)(C)C.C([O-])(O)=O.[Na+]>O>[OH:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH:17]=[C:18]2[C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)=[CH:13][C:12]=1[O:34][CH3:35]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 181883597-[(Tertbutyldimethylsilyl)oxy]-1-hydroxy-6-methoxy-1-(3',4',5'-trimethoxyphenyl)-tetralin

Product 1

HCID 10132157HCID 10132157, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of acetic acid (10 mL) in H2O (60 mL), was added 7-[(tertbutyldimethylsilyl)oxy]-1-hydroxy-6-methoxy-1-(3′,4′,5′-trimethoxyphenyl)-tetralin (137 mg, 0.29 mmol). The solution was heated to reflux for 8 hour, and then cooled down to rt. NaHCO3 (20 mL, saturated solution) was added, and the mixture was partitioned between CH2Cl2 and water. The organic layer was dried over anhydrous sodium sulfate, and after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 7-Hydroxy-6-methoxy-1-(3′,4′,5′-trimethoxyphenyl)-3,4-dihydronaphthalene (84.3 mg, 0.25 mmol, 86%) was obtained following purification by column chromatography. 1H-NMR (CDCl3, 300 MHz) 2.37 (m, 2H), 2.78 (t, J=7.7 Hz, 2H), 3.84 (s, 6H), 3.88 (s, 3H), 3.91 (s, 3H), 5.41 (s, 1H), 5.98 (t, J=4.6 Hz, 1H), 6.54 (s, 2H), 6.68 (s, 1H), 6.81 (s, 1H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 8 hour
  3. customthe mixture was partitioned between CH2Cl2 and water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationafter filtration
  6. concentrationthe organic layer was concentrated in vacuo
  7. customto provide a yellow oil

Sources & evidence

ORD record
ord-5bb4f4c6b2af482091e34d66f90f365b
Source dataset
uspto-grants-2003_07
Patent number
US06593374B2

Reaction notes

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