Methanol → HCID 68539933, compound

HRID 1992953Notes

Reaction equation

HRID 1992953 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[O:29][C:30]3[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-]#N.[Na+].[CH3:41][OH:42]>C(Cl)Cl.CCOC(C)=O.O=[Mn]=O>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[C:24]([C:25]([F:27])([F:26])[F:28])=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]=3[O:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([O:42][CH3:41])=[O:35])=[CH:36][CH:37]=3)=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 86616665HCID 86616665, compound

Product 1

HCID 68539933HCID 68539933, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-{[2-{4-[(phenylmethyl)oxy]phenyl}-3-(trifluoromethyl)-1-naphthalenyl]oxy}benzaldehyde (187) (0.23 g, 0.45 mmol) in MeOH (4 mL) and CH2Cl2 (2 mL) was added NaCN (0.12 g, 2.26 mmol) followed by MnO2 (0.56 g, 5.42 mmol). The reaction mixture was stirred at room temperature overnight, diluted with EtOAc (50 mL) and filtered through a pad of celite on top of a layer of silica gel. The filtrate was washed with water, brine, dried over Na2SO4, filtered, and concentrated to give the crude product as a light yellow solid, which upon trituration with 1% MeOH in hexanes, gave 0.21 g (86%) of the title compound (188) as a white solid. mp 131-132° C. 1H NMR (400 MHz, CDCl3): δ 3.85 (s, 3H), 5.01 (s, 2H), 6.58 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 7.05 (d, J=8.6 Hz, 2H), 7.30-7.44 (m, 5H), 7.55-7.66 (m, 2H), 7.79 (d, J=8.8 Hz, 2H), 7.89 (d, J=8.2 Hz, 1H), 8.03 (d, J=8.1 Hz, 1H), 8.24 (s, 1H). LCMS (ESI): m/z 551 (M+Na)+.

Workup

  1. filtrationfiltered through a pad of celite on top of a layer of silica gel
  2. washThe filtrate was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product as a light yellow solid, which upon trituration with 1% MeOH in hexanes

Sources & evidence

ORD record
ord-3bc2e05f9b964debad0dfdd8512e0565
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…