HCID 22324922, compound → HCID 22324979, compound

HRID 496425Notes

Reaction equation

HRID 496425 reaction equation
[OH:1][CH2:2][C:3]([CH3:25])([CH3:24])[O:4][C:5]1[C:6]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([OH:15])[CH2:10][CH2:9][CH2:8]2>[O-2].[O-2].[Mn+4].O1CCCC1>[OH:1][CH2:2][C:3]([CH3:25])([CH3:24])[O:4][C:5]1[C:6]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2

Participants

4

Reactant 1

HCID 22324922HCID 22324922, compound

Product 1

HCID 22324979HCID 22324979, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(2-hydroxy-1,1-dimethylethoxy)-5-(2-phenylethyl)-1,2,3,4-tetrahydro-1-naphthalenol (0.756 g, 2.22 mmol), tetrahydrofuran (5 mL), and manganese dioxide (4.6 g) was stirred for 4 h. The mixture was filtered through Celite and the filter cake was washed thoroughly with dichloromethane. The combined filtrates were concentrated to give 6-(2-hydroxy-1,1-dimethylethoxy)-5-(2-phenylethyl)-3,4-dihydro-1(2H)-naphthalenone as a pale yellow solid, 0.656 g, 87% yield. NMR spectrum was consistent with structure. Calcd. for C22H26O3: Theory: C, 78.08; H, 7.74. Found: C, 77.90; H, 7.75. 4. 2-Methyl-2-{[5-oxo-1-(2-phenylethyl)-5,6,7,8-tetrahydro-2-naphthalenyl]oxy}propyl trifluoromethanesulfonate

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed thoroughly with dichloromethane
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-11e608be52604275a86021b12a16c6e3
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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