Pyridine → [2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl acetate

HRID 494659Notes

Reaction equation

HRID 494659 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:18][OH:19])([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](OC(=O)C)(=[O:22])[CH3:21].N1C=CC=CC=1>O>[C:20]([O:19][CH2:18][C:4]1([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH:12]=[C:3]1[O:2][CH3:1])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68871071[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methanol

Product 1

HCID 68872462[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl acetateYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 179A (0.18 g, 0.7 mmol), acetic anhydride (0.2 mL), and pyridin (1 mL) was stirred at room temperature for 18 h. The solution was diluted with water (3 mL) and extracted with ethyl acetate (2× 1 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (hexane to 5% ethyl acetate/hexane) afforded product as a colorless oil (0.17 g, 81%). 1H NMR (300 MHz, CDCl3) δ ppm 0.66 (m, 1H), 0.76 (dd, J=9.56, 6.62 Hz, 6H), 0.89 (m, 1H), 1.38 (m, 1H), 1.61 (m, 1H), 1.81 (s, 3H), 1.95 (m, 1H), 3.50 (s, 2H), 3.58 (s, 3H), 4.24 (d, J=10.66 Hz, 1H), 4.42 (d, J=10.66 Hz, 1H), 5.01 (t, J=3.49 Hz, 1H), 7.20 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate (2× 1 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37d9b5aab7394de896e5a43d1f195122
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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