2-Naphthol → HCID 25016430, compound

HRID 1034574Notes

Reaction equation

HRID 1034574 reaction equation
[OH:1][C:2]([CH2:4][C:5]1[C:6](=[O:17])[CH2:7][CH:8]([O:10]C2CCCCO2)[CH:9]=1)=[O:3].[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1O.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH:26]1[C:27]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:25]=1[O:1][C:2]([CH2:4][C:5]1[C:6](=[O:17])[CH2:7][CH:8]([OH:10])[CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 10868DicyclohexylcarbodiimideHCID 25016429HCID 25016429, compound

Product 1

HCID 25016430HCID 25016430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 g of 2-Hydroxycarbonylmethyl-4-tetrahydropyranyloxy-2-cyclopenten-1-one (21 mmol) obtained from Example 5, 2-naphthol (4.7 g, 32 mmol), dichloromethane (50 ml), and 0.2 g 4-(dimethylamine)pyridine were added together to a 50 ml dichloromethane solution containing 1,3-dicyclohexylcarbodiimide (7 g, 34 mmol). The reaction mixture was stirred at room temperature for about 4 hours. The precipitate was filtered off. The filtrate was washed with 20 ml of diluted hydrochloride solution, water, dried over anhydrous magnesium sulfate, filtered, and evaporated under vacuum. The crude product was dissolved in 30 ml acetone and 6 ml water, further added with 0.3 g p-toluenesulfonic acid and stirred overnight. Upon completion of the reaction, acetone was evaporated and the reaction mixture was diluted with ethyl acetate and washed with an aqueous sodium bicarbonate solution and a brine solution. The organic liquid was subjected to the previous work-up procedure, including dehydration, filtration, and evaporation, and purification by chromatography on silica gel to obtain the title compound as white solid. MP: 81° C. (4.2 g, 71%) 1H-NMR (CDCl3/TMS): δ 7.82 (m,2H), 7.78 (d, 1H), 7.55 (m,2H), 7.46 (m,2H), 7.21 (dd, 1H), 5.04 (m, 1H), 3.56 (s, 2H), 2.89 (dd, 1H), 2.38 (dd, 1H), 1.60 (brs, 1H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washThe filtrate was washed with 20 ml of diluted hydrochloride solution, water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. dissolutionThe crude product was dissolved in 30 ml acetone
  7. addition6 ml water, further added with 0.3 g p-toluenesulfonic acid
  8. stirringstirred overnight
  9. customUpon completion of the reaction, acetone
  10. customwas evaporated
  11. additionthe reaction mixture was diluted with ethyl acetate
  12. washwashed with an aqueous sodium bicarbonate solution
  13. filtrationdehydration, filtration, and evaporation, and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-d2aa042e53c14262892672fbda5ffb4d
Source dataset
uspto-grants-2013_10
Patent number
US08546114B2

Reaction notes

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