Toluene → Methyl 2-[3-vinyl-4-(quinolin-2-yl-methoxy)phenyl]acetate

HRID 1464390Notes

Reaction equation

HRID 1464390 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.[C:25]1(C)C=CC=C[CH:26]=1>>[CH:25]([C:2]1[CH:3]=[C:4]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)=[CH2:26]

Participants

3

Reactant 2

HCID 1140TolueneHCID 19087791Methyl 2-[3-bromo-4-(quinolin-2-yl-methoxy)phenyl]acetate

Product 1

HCID 19087790Methyl 2-[3-vinyl-4-(quinolin-2-yl-methoxy)phenyl]acetate

Procedure

200 mg (0.21 mmol) of the catalyst [P(phenyl)3 ]4Pd are weighed into a 50 ml brown glass flask (flushed with argon) and 2 g (5.2 mmol) of the compound from Example XX and 1.4 ml (5.2 mmol) of Bu3SnCH=CH2 (d=1.086), both dissolved in 10 ml of toluene, are added under argon. The mixture is heated to boiling for 20 hours with stirring in a light-protected apparatus. The solvent is then evaporated in vacuo and the residue is separated by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=4:1).

Workup

  1. additionare added under argon
  2. temperatureThe mixture is heated
  3. customThe solvent is then evaporated in vacuo
  4. customthe residue is separated by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-93a2ff1c48dc4803ae1e4ab7a7d11f0c
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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