Cornforth reagent → HCID 25065364, compound

HRID 555248Notes

Reaction equation

HRID 555248 reaction equation
[Mg].BrC1C=C(OC)C(OC)=C(C2OCCCO2)C=1.[O:19]1[CH2:24][CH2:23][CH2:22][O:21][CH:20]1[C:25]1[CH:26]=[C:27]([CH:35]([C:37]2[CH:42]=[C:41]([C:43]3[O:44][CH:45]=[CH:46][CH:47]=3)[CH:40]=[CH:39][C:38]=2[O:48][CH3:49])[OH:36])[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[O:19]1[CH2:24][CH2:23][CH2:22][O:21][CH:20]1[C:25]1[CH:26]=[C:27]([C:35]([C:37]2[CH:42]=[C:41]([C:43]3[O:44][CH:45]=[CH:46][CH:47]=3)[CH:40]=[CH:39][C:38]=2[O:48][CH3:49])=[O:36])[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32]

Participants

7

Reactant 4

HCID 2724130Cornforth reagentHCID 5462224MagnesiumHCID 15054922HCID 15054922, compoundHCID 66987832HCID 66987832, compound2×

Product 1

HCID 25065364HCID 25065364, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

As shown in Reaction 1, first, magnesium was added to 2-(5-bromo-2,3-dimethoxyphenyl)-1,3-dioxane as a starting material, which substituted an aldehyde group with an acetyl group. Then, Compound (III) derivative was substituted thereto to synthesize (3-(1,3-dioxan-2-yl)-4,5-dimethoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanol. Thus obtained (3-(1,3-dioxan-2-yl)-4,5-dimethoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanol (1.7 g, 4.0 mmol) was dissolved in 40 ml of anhydrous dichloromethane, whereto 4 Å molecular sieves (0.6 g) and pyridinium dichromate (PDC) (2.24 g, 6.0 mmol) were added sequentially at 0° C. The mixture was reacted at room temperature for 24 hours. After completion of the reaction, diethylether (150 ml) was added to the reaction mixture, and the precipitates were filtered off using Celite. An organic layer was extracted out from the filtrate using brine, and the organic layer was dried over Na2 SO3. The solvent was removed, and the resulting residue was purified by column chromatography (SiO2, n-Hex/EA=1/1) to synthesize Compound 233 (1.02 g, 60%).

Workup

  1. customAs shown in Reaction 1
  2. customThe mixture was reacted at room temperature for 24 hours
  3. additionwas added to the reaction mixture
  4. filtrationthe precipitates were filtered off
  5. extractionAn organic layer was extracted out from the filtrate
  6. customthe organic layer was dried over Na2 SO3
  7. customThe solvent was removed
  8. customthe resulting residue was purified by column chromatography (SiO2, n-Hex/EA=1/1)
  9. customto synthesize Compound 233 (1.02 g, 60%)

Sources & evidence

ORD record
ord-5d5712f3af7944d0b0f01d4b23df004d
Source dataset
uspto-grants-2011_11
Patent number
US08053439B2

Reaction notes

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