Tetrahydrofuran → HCID 86682691, compound

HRID 449788Notes

Reaction equation

HRID 449788 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6]1([C:12]2[CH:18]=[CH:17][C:15]([OH:16])=[CH:14][C:13]=2[OH:19])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[H-].[Na+].[P:22](Cl)([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O>[CH2:5]([O:1][P:22]([O:16][C:15]1[CH:17]=[CH:18][C:12]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)=[C:13]([O:19][P:22]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH:14]=1)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C:4]1[CH:33]=[CH:34][CH:35]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 750554-CyclohexylresorcinolHCID 4641201(Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

Product 1

HCID 86682691HCID 86682691, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran solution (10 ml) of 4-cyclohexylresorcinol (926 mg), sodium hydride (60% dispersion in liquid paraffin) (404 mg) was added and stirred at 0° C. for 30 minutes. Then, dibenzyl chlorophosphate (10 w/v % solution in benzene) (30 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 (4.12 g) was subjected to silica gel chromatography (silica gel 90 g, chloroform to chloroform:methanol=100:1), to give 1,3-bis(dibenzylphosphonooxy)-4-cyclohexylbenzene (2.19 g, yield: 64%) as a yellow liquid.

Workup

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

Sources & evidence

ORD record
ord-e3fe8978e03448e5b19ee71f2e107697
Source dataset
uspto-grants-2013_07
Patent number
US08486919B2

Reaction notes

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