Ethanol → [2-(4,5-Dibenzoyl-tetrahydro-furan-2-yl)-vinyl]-phosphonic acid diethyl ester

HRID 2191013Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH:9]=[CH:10][CH:11]1[CH2:15][CH:14](O)[CH:13](O)[O:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:27][CH2:28][OH:29]>N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH:9]=[CH:10][CH:11]1[CH2:15][CH:14]([C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]([C:28](=[O:29])[C:27]2[CH:14]=[CH:15][CH:11]=[CH:10][CH:9]=2)[O:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

Compound 9.7 (3.1 g, 11.8 mmol) in pyridine (15 mL) was treated with benzoyl chloride (4.0 mL, 35 mmol) dropwise and the mixture was stirred at 45° C. for 1 h (significant exotherm upon BzCl addition). The mixture was cooled to 0° C. and EtOH (2 mL) was added dropwise and stirred for 10 minutes. The solution was concentrated in vacuo and the residue was dissolved in EtOAc (100 mL) and washed with 1 N HCl (10 mL) and brine (10 mL). The solution was dried over MgSO4, filtered, and concentrated in vacuo. The residue was treated to silica gel column chromatography (SiO2, 4×20 cm, 50-100% EtOAc-hexanes gradient) to afford compound 9.8 (4.2 g, 75% yield).

Workup

temperatureThe mixture was cooled to 0° C.
stirringstirred for 10 minutes
concentrationThe solution was concentrated in vacuo
dissolutionthe residue was dissolved in EtOAc (100 mL)
washwashed with 1 N HCl (10 mL) and brine (10 mL)
dry with materialThe solution was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
additionThe residue was treated to silica gel column chromatography (SiO2, 4×20 cm, 50-100% EtOAc-hexanes gradient)

Sources & evidence

ORD record: ord-5848e5c60b90488ba10e28fe8d3ec2e3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324179B2

Reaction notes

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