Triethylsilane → HCID 23147385, compound

HRID 495305Notes

Reaction equation

HRID 495305 reaction equation
C([SiH](CC)CC)C.[Br:8][C:9]1[C:10]([CH2:34][C:35]([O:37][CH3:38])=[O:36])=[C:11]([C:23]2[O:27][C:26]([CH:28]=[CH:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][CH:24]=2)[C:12]([O:19][CH2:20][O:21][CH3:22])=[CH:13][C:14]=1[O:15][CH2:16][O:17][CH3:18]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C1(C)C=CC=CC=1>[Br:8][C:9]1[C:10]([CH2:34][C:35]([O:37][CH3:38])=[O:36])=[C:11]([C:23]2[O:27][C:26]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][CH:24]=2)[C:12]([O:19][CH2:20][O:21][CH3:22])=[CH:13][C:14]=1[O:15][CH2:16][O:17][CH3:18]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 74020637HCID 74020637, compound

Product 1

HCID 23147385HCID 23147385, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In an argon atmosphere, triethylsilane (0.15 mL, 0.94 mmol) and tris(triphenylphosphine)rhodium(I) chloride (30 mg, 0.032 mmol) were added to toluene (2.0 mL) solution of methyl 3-{5-[3-bromo-2-(methoxycarbonylmethyl)-4,6-bis(methoxymethoxy)phenyl]furan-2-yl}acrylate (89 mg, 0.18 mmol) obtained in the above, and stirred at 50° C. for 3 hours. The reaction solution was concentrated, and the residue was purified through silica 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}propanoate. Then, the resulting compound was dissolved in methanol solution (5.0 mL) of 10% hydrochloric acid, stirred at room temperature for 2 hours, and then concentrated under reduced pressure. The resulting residue was purified through preparative thin-layer chromatography (methanol/chloroform=1/9) to obtain Compound 267 (35 mg, 48%).

Workup

  1. customobtained in the above, and
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified through silica chromatography (n-hexane to ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-6c2adf5d2506423d87f744aec16bf34b
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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