Phenol → HCID 20448802, compound

HRID 358366Notes

Reaction equation

HRID 358366 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][C:11](=[O:13])[C:10]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:9]1.[C:23]1(O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][C:11](=[O:13])[C:10]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:21])=[CH:9]1

Participants

7

Reactant 4

HCID 996PhenolHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 20448804HCID 20448804, compound

Product 1

HCID 20448802HCID 20448802, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

686 mg (2.09 mmoles) of 4(RS)-tetrahydropyranyloxy-2-(5-carboxypentylthio)-2-cyclopentenone and 295 mg (3.14 mmoles) of phenol were dissolved in 10 ml of dichloromethane, and 0.1 ml of pyridine was added. To the solution was added 10 ml of a dichloromethane solution of 860 mg (4.18 mmoles) of dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 18 hours. After the reaction, ethyl acetate was added to the reaction mixture. The organic layer was washed successively with an aqueous solution of sodium bicarbonate, an aqueous solution of potassium bisulfate, and an aqueous solution of sodium chloride, dried, and then concentrated. The residue was chromatographed on a silica gel column using hexane/ethyl acetate (7/2) as an eluent to give 653 mg (1.62 mmoles; yield 77.3%) of 4(RS)-tetrahydropyranyloxy-2-(5-phenoxycarbonylpentylthio)-2-cyclopentenone.

Workup

  1. additionwas added to the reaction mixture
  2. washThe organic layer was washed successively with an aqueous solution of sodium bicarbonate
  3. dry with materialan aqueous solution of potassium bisulfate, and an aqueous solution of sodium chloride, dried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-a59875a6ff6f44be95534d27e2984940
Source dataset
uspto-grants-1984_08
Patent number
US04466980

Reaction notes

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