2-(Tributylstannyl)furan → 2-(6-Methoxy-1-methoxymethoxy-3-methyl-naphthalen-2-yl)-furan

HRID 1992969Notes

Reaction equation

HRID 1992969 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)CCC.Br[C:20]1[C:29]([CH3:30])=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:31][CH3:32])[CH:26]=2)[C:21]=1[O:33][CH2:34][O:35][CH3:36]>C1(C)C=CC=CC=1.CCOCC.O.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:32][O:31][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[C:21]([O:33][CH2:34][O:35][CH3:36])=[C:20]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[C:29]([CH3:30])=[CH:28]2

Participants

7

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene2×

Product 1

HCID 685396222-(6-Methoxy-1-methoxymethoxy-3-methyl-naphthalen-2-yl)-furanYield 76%

Reagents, catalysts & solvents 4

HCID 178420553HCID 178420553, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
105 °C

Procedure

2-(Tributylstannyl)-furan (0.4 mL, 1.29 mmol)) was added slowly to a solution of 2-bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (14 (0.4 g, 1.29 mmol) in toluene (10 mL). Reaction mixture was heated at 105° C. A portion (0.01 g) of tetrakis(triphenylphosphino)palladium (0) (0.061 g, 0.053 mmol) was added every 1 h until reaction was complete. Reaction mixture was cooled to RT then diluted with Et2O and water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude oil was purified with a gradient of 20% EtOAc in hexanes to give 0.29 g (76%) of the title compound (213) as oil. 1H NMR (400 MHz, d-CDCl3): δ 2.36 (s, 3H), 3.37 (s, 3H), 3.93 (s, 3H), 4.85 (s, 2H), 6.49-6.50 (m, 1H), 6.53-6.55 (m, 1H), 7.05 (m, 1H), 7.11 (dd, J1=2.4 Hz, J2=9.2 Hz, 1H), 7.39 (s, 1H), 7.58-7.58 (m, 1H), 8.08 (d, J=9.2 Hz, 1H).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperaturewas cooled to RT
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude oil was purified with a gradient of 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-9bf772612e05454888232bcbc75a2c9e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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