Cyclopentanol → HCID 68458192, compound

HRID 501768Notes

Reaction equation

HRID 501768 reaction equation
[OH:1][C:2]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11](=[O:16])[CH2:10][CH2:9]2)=[O:5].[CH:22]1(O)[CH2:26][CH2:25][CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O>[CH:22]1([O:21][C:19]2[CH:18]=[CH:17][C:3]([C:4]([C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[O:12][C:11](=[O:16])[CH2:10][CH2:9]4)=[O:5])=[C:2]([OH:1])[CH:20]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 7298CyclopentanolHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 23021508HCID 23021508, compound

Product 1

HCID 68458192HCID 68458192, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 75555Diisopropyl diazene-1,2-dicarboxylateSolvent

Procedure

50.0 g of 6-(2,4-dihydroxybenzoyl)-2-chromanone, 17.6 mL of cyclopentanol, and 55.4 g of triphenylphosphine were dissolved in 500 mL of tetrahydrofuran, to which 41.6 mL of diisopropyl azodicarboxylate was added dropwise at temperatures of 15 to 32° C., and this solution was stirred for 30 minutes at room temperature. The reaction mixture was poured into a mixture of ethyl acetate and water for the separation of the organic phase therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate and the solvent was distilled out thereof under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1] to yield 54.7 g of 6-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-chromanone as light yellow solid.

Workup

  1. additionwas added dropwise at temperatures of 15 to 32° C.
  2. washAfter the resultant organic phase was washed with water
  3. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled out thereof under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1]

Sources & evidence

ORD record
ord-13eb4a06236c4c58b2f1d41837ab3e68
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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