Methanol → HCID 11995949, compound

HRID 495189Notes

Reaction equation

HRID 495189 reaction equation
C([O:4][C:5]1[C:6]([C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)C=C.B(Br)(Br)Br.CCCCCC.CO>ClCCl>[CH2:12]([O:11][C:9]1[CH:10]=[C:5]([OH:4])[C:6]([C:20](=[O:29])[C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=1)[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 25134Boron tribromideHCID 23116478HCID 23116478, compound

Product 1

HCID 11995949HCID 11995949, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 3,5-diallyloxy-2-(4-methoxybenzoyl)phenylacetate (100 mg, 0.25 mmol) obtained in Example 15, Step 1 was dissolved in dichloromethane (10 mL). After the solution was cooled to −78° C., a 1.0 mol/L solution of boron tribromide in hexane (0.50 mL, 0.5 mmol) was added thereto, followed by stirring at −78° C. for 30 minutes. To the reaction mixture were successively added methanol and a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The organic layer was dried anhydrous over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=20/1) to obtain Compound 18 (54 mg, 61%).

Workup

  1. extractiona saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-399eabf9e3634ca69559ce8e9d3c9377
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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