Ethyl Acetate → HCID 57708981, compound

HRID 546818Notes

Reaction equation

HRID 546818 reaction equation
[Mg].[CH2:2]([O:4][C:5](=[O:47])/[CH:6]=[CH:7]/[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH:32]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:26]([CH3:45])[CH:25]=3)([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:46])=[CH:11][CH:12]=1)C.C(OCC)(=O)C.S(=O)(=O)(O)[O-].[K+]>CO.O1CCCC1>[CH3:2][O:4][C:5](=[O:47])[CH2:6][CH2:7][C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH:32]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:26]([CH3:45])[CH:25]=3)([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:46])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 5462224MagnesiumHCID 57708944HCID 57708944, compound

Product 1

HCID 57708981HCID 57708981, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (24.3 mg, 1.0 mmol) was added to a solution of (E)-3-{5-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-furan-2-yl}-acrylic acid ethyl ester (Example 5-(1); 64.5 mg, 0.10 mmol) in methanol (2 mL) and tetrahydrofuran (0.5 mL) at room temperature, and the mixture was stirred at the same temperature for two hours. Ethyl acetate and a potassium bisulfate aqueous solution were added to the reaction mixture to separate the layers. Then, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=10/1) to give the title compound (48 mg, 76%).

Workup

  1. customto separate the layers
  2. washThen, the organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-4bafe02c804240089fc6bb96aed6ec1f
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…