HCID 86697490, compound → HCID 44547456, compound

HRID 516857Notes

Reaction equation

HRID 516857 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2([CH:15]=[O:16])[CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1.CC(C)=[O:24].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.CCOC(C)=O>[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2([C:15]([OH:24])=[O:16])[CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 86697490HCID 86697490, compoundHCID 131709961Jones' reagent

Product 1

HCID 44547456HCID 44547456, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(3-(2,6-Dimethylbenzyloxy)phenyl)cyclopropanecarbaldehyde (Step D, 3.5 g, 12.5 mmol) in acetone (50 ml) was added drop wise jones reagent (15 ml) at room temperature. The reaction mixture was stirred for 6 hours, diluted in EtOAc and washed with water, brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to give the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-c532acae482141ffbc6f689750d0aecd
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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