HCID 54561798, compound → HCID 74020637, compound

HRID 495304Notes

Reaction equation

HRID 495304 reaction equation
[C:1]([CH:5]=C1CCP(C2C=CC=CC=2)C1(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH3:4])=[O:2].[Br:29][C:30]1[C:35]([O:36][CH2:37][O:38][CH3:39])=[CH:34][C:33]([O:40][CH2:41][O:42][CH3:43])=[C:32]([C:44]2[O:45][C:46]([CH:49]=O)=[CH:47][CH:48]=2)[C:31]=1[CH2:51][C:52]([O:54][CH3:55])=[O:53]>C1(C)C=CC=CC=1>[Br:29][C:30]1[C:31]([CH2:51][C:52]([O:54][CH3:55])=[O:53])=[C:32]([C:44]2[O:45][C:46]([CH:49]=[CH:5][C:1]([O:3][CH3:4])=[O:2])=[CH:47][CH:48]=2)[C:33]([O:40][CH2:41][O:42][CH3:43])=[CH:34][C:35]=1[O:36][CH2:37][O:38][CH3:39]

Participants

4

Reactant 2

HCID 54561798HCID 54561798, compoundHCID 86613502HCID 86613502, compound

Product 1

HCID 74020637HCID 74020637, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

(Carbomethoxymethylene)triphenylphospholane (0.17 g, 0.51 mmol) was added to toluene (4.0 mL) solution of methyl 2-bromo-6-(5-formylfuran-2-yl)-3,5-bis(methoxymethoxy)phenylacetate (0.11 g, 0.25 mmol) obtained in the step 3 in Example 265, and stirred at 60° C. for 4 h ours. The reaction solution was cooled to room temperature, and then concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/2) to obtain methyl 3-{5-[3-bromo-2-(methoxycarbonylmethyl)-4,6-bis(methoxymethoxy)phenyl]furan-2-yl}acrylate (0.12 g, 93%).

Workup

  1. customobtained in the step 3 in Example 265
  2. temperatureThe reaction solution was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-33da08872b834b0d893c2d15c1a4b039
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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