Trimethyl orthoformate → 1-Allyl-1-methyl-1,4-dihydronaphthalen-2-yl methyl ether

HRID 494626Notes

Reaction equation

HRID 494626 reaction equation
[CH2:1]([C:4]1([CH3:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]1=[O:14])[CH:2]=[CH2:3].[CH3:16]OC(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:16][O:14][C:5]1[C:4]([CH2:1][CH:2]=[CH2:3])([CH3:15])[C:13]2[C:8]([CH2:7][CH:6]=1)=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 152546301-allyl-1-methyl-3,4-dihydronaphthalen-2(1H)-one

Product 1

HCID 688737961-Allyl-1-methyl-1,4-dihydronaphthalen-2-yl methyl etherYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 123A (10.1 g, 50.5 mmol), trimethylorthoformate (20 mL), p-toluenesulfonic acid monohydrate (60 mg, 0.315 mmol) in methanol (100 mL) was heated at 60 C for 2 hours. After cooling to room temperature, the solution was concentrated in vacuo, and the resultant residue was purified by column chromatography employing 70-230 mesh silica gel eluting with hexane to provide the title compound as a colorless oil (7.8 g, 73%). 1H NMR (300 MHz, DMSO-d6): δ 1.38 (s, 3H), 2.44 (dd, J=13.8, 7.4 Hz, 1H), 2.65 (dd, J=13.6, 7.0 Hz, 1H), 3.41 (d, J=3.7 Hz, 2H), 3.54 (s, 3H), 4.75 (m, 2H), 4.90 (t, J=3.7 Hz, 1H), 5.24 (m, 1H), 7.10 (m, 2H), 7.19 (m, 1H), 7.40 (d, J=7.8 Hz, 1H).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customthe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-58301ca8ef684e83ad5f28666dd5911f
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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