Tetrahydrofuran → HCID 86682690, compound

HRID 449786Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6]([C:9]1[CH:15]=[CH:14][C:12]([OH:13])=[CH:11][C:10]=1[OH:16])([CH3:8])[CH3:7].[H-].[Na+].[P:19](Cl)([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O>[CH2:5]([O:1][P:19]([O:13][C:12]1[CH:14]=[CH:15][C:9]([CH:6]([CH3:8])[CH3:7])=[C:10]([O:16][P:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:11]=1)([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:4]1[CH:30]=[CH:31][CH:32]=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a tetrahydrofuran solution (10 ml) of 4-isopropylresorcinol (466 mg), sodium hydride (60% dispersion in liquid paraffin) (269 mg) was added and stirred at 0° C. for 30 minutes. Then, dibenzyl chlorophosphate (10 w/v % solution in benzene) (20 ml) was added dropwise. After stirring at room temperature for 3 hours, water (30 ml) was added to the reaction mixture, and the extraction was carried out with ethyl acetate (30 ml). Then, the extract was washed with saturated brine (20 ml), dried with anhydrous sodium sulfate and then concentrated. The residue (2.23 g) was subjected to silica gel chromatography (silica gel 76 g, chloroform to chloroform:methanol=70:1), to give 1,3-bis(dibenzylphosphonooxy)-4-isopropylbenzene (1.71 g, yield: 83%) as a yellow liquid.

Workup

stirringAfter stirring at room temperature for 3 hours
extractionthe extraction
washThen, the extract was washed with saturated brine (20 ml)
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-06ef22596580407d9d66f20315f33726
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486919B2

Reaction notes

Loading…