Diethyl Ether → HCID 13746902, compound

HRID 1732026

Reaction equation

HRID 1732026 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[O:1]=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13746901Methyl 7-hydroxy-7-[2-(phenylmethyl)phenyl]-5-heptynoateHCID 178418287HCID 178418287, compound

Product 1

HCID 13746902HCID 13746902, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 0.3 g (0.93 mmol) methyl 7-hydroxy-7-[2-(phenylmethyl)phenyl]-5-heptynoate in 20.0 ml methylene chloride at room temperature was added 0.5 g (2.32 mmol) of pyridinium chlorochromate (PCC). The mixture was stirred for 2 hours and 80.0 ml of diethylether was added to the reaction mixture. The reaction mixture was filtered through Florisil® brand magnesium silicate evaporated to an oil and purified by flash chromatography to give the title compound in 67% yield (200 mg; 0.625 mmol). NMR (CDCl3, 200 MHz) δ: 2.0 (m, 2H), 2.5 (m, 4H), 3.67 (s, 3H), 4.40 (s, 2H), 7.12-8.25 (m, 9H). Mass spectrum: m/z=320 (M+).

Workup

  1. filtrationThe reaction mixture was filtered through Florisil® brand magnesium silicate
  2. customevaporated to an oil
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7ee64b06b4ca48c2934ad289384ebbe7
Source dataset
uspto-grants-1986_11
Patent number
US04624964

Linked notes

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