Triacetoxyperiodinane → 2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalene-1-carbaldehyde

HRID 2224985Notes

Reaction equation

HRID 2224985 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.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:1][O:2][C:3]1[C:4]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])([CH:18]=[O:19])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68871071[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methanol

Product 1

HCID 876087112-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalene-1-carbaldehydeYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 179A (0.6 g, 2.3 mmol) in dichloromethane (15 mL) was added Dess-Martin periodanate (1.5 g, 3.5 mmol). The solution was stirred at room temperature for 18 h and then concentrated in vacuo. Column chromatography on silica (10%-20%-30% dichloromethane/hexane) afforded product as a light yellow oil (0.32 g, 53%). 1H NMR (300 MHz, CDCl3) δ ppm 0.63 (m, 1 H), 0.76 (dd, J=12.13, 6.62 Hz, 6 H), 0.92 (m, 1 H), 1.41 (m, 1 H), 1.93 (m, 1 H), 2.18 (m, 1 H), 3.59 (m, 5 H), 5.19 (t, J=3.68 Hz, 1 H), 7.01 (m, 1 H), 7.21 (m, 3 H), 9.40 (s, 1 H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8569231ddf5743478009fa2b86bd5a9f
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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