3,4-dihydro-2H-pyran → HCID 22345015, compound

HRID 1748920Notes

Reaction equation

HRID 1748920 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH3:9])=[CH:4][CH:3]=1.[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1>C(OCC)(=O)C.FC(F)(F)C(O)=O>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]1[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:24]3)=[CH:12][CH:11]=2)([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH:29]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)=[CH:21][CH:22]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 931181,1,1-Tris(4-hydroxyphenyl)ethane

Product 1

HCID 22345015HCID 22345015, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.53 g (8.26 mmol) of 1,1,1-tris(4-hydroxyphenyl)ethane was dissolved in 20 mL of ethyl acetate in a round bottom flask. 8 mL of 2,3-dihydropyran and 8 drops of trifluoroacetic acid were added to the mixture. After stirring overnight, a white precipitate had formed in the flask. This precipitate was collected by filtration and dissolved in 20 mL of dichloromethane to which was added 8 mL of 2,3-dihydropyran and 6 drops of trifluoroacetic acid. After stiffing for two days, 20 mL of 0.261 N TMAH was added; the organic phase was extracted, washed with water (20 mL) twice, and dried with MgSO4. The solvent was removed in vacuo to yield 2.82 g of THPE-THP as a white powder. Yield: 77%. 1H-NMR (300 MHz, CDCl3) δ (ppm) 1.5-2.0 (18H), 2.09 (3H), 3.60 (3H), 3.92 (3H), 5.37 (3H), 6.91 (6H), 6.98 (6H).

Workup

  1. customa white precipitate had formed in the flask
  2. filtrationThis precipitate was collected by filtration
  3. dissolutiondissolved in 20 mL of dichloromethane to which
  4. additionwas added 8 mL of 2,3-dihydropyran and 6 drops of trifluoroacetic acid
  5. waitAfter stiffing for two days
  6. addition20 mL of 0.261 N TMAH was added
  7. extractionthe organic phase was extracted
  8. washwashed with water (20 mL) twice
  9. dry with materialdried with MgSO4
  10. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-92f859225e214cb9972a650ecac093a3
Source dataset
uspto-grants-2015_10
Patent number
US09152043B2

Reaction notes

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