Oxalyl chloride → 6-(Methyloxy)-3-(3,3,3-trifluoropropyl)-3,4-dihydro-1(2H)-naphthalenone

HRID 1992902Notes

Reaction equation

HRID 1992902 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][CH2:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:6][C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[C:7](=[O:9])[CH2:6][CH:5]([CH2:4][CH2:3][C:2]([F:1])([F:20])[F:19])[CH2:10]2

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 685398486,6,6-Trifluoro-3-{[3-(methyloxy)phenyl]methyl}hexanoic acid

Product 1

HCID 685362636-(Methyloxy)-3-(3,3,3-trifluoropropyl)-3,4-dihydro-1(2H)-naphthalenoneYield 73%

Procedure

6,6,6-Trifluoro-3-{[3-(methyloxy)phenyl]methyl}hexanoic acid (120) (1.56 g, 5.38 mmol) was treated with oxalyl chloride followed by AlCl3 in CH2Cl to give 1.07 g (73%) of the title compound (121) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.65-1.75 (m, 2H), 2.10-2.35 (m, 4H), 2.65-2.80 (m, 2H), 2.90-3.05 (m, 1H), 3.85 (s, 3H), 6.70 (d, J=2.4 Hz, 1H), 6.84 (dd, J1=8.8 Hz, J2=2.5 Hz, 1H), 7.99 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 273 (M+H)+.

Sources & evidence

ORD record
ord-226fd7057b984c9390f73aa8dae15468
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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