Methanol → HCID 11995949, compound

HRID 499878Notes

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

Conditions

Temperature: -78 °C

Procedure

Methyl 3,5-diallyloxy-2-(4-methoxybenzoyl)phenyl-acetate (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 over anhydrous 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

extractiona saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record: ord-c2b18a7a9d2b4010941510125b2dfbb8
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767693B2

Reaction notes

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