HCID 73028854, compound → HCID 72991640, compound

HRID 868797Notes

Reaction equation

HRID 868797 reaction equation
[OH:1][CH2:2][CH:3]=[C:4]([CH3:29])[CH:5]=[CH:6][C:7]1([OH:28])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[N:17][N:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[CH2:23][O:24][CH3:25])[CH2:9][C:8]1([CH3:27])[CH3:26]>CC(C)=O.O=[Mn]=O>[OH:28][C:7]1([CH:6]=[CH:5][C:4]([CH3:29])=[CH:3][CH:2]=[O:1])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[N:17][N:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[CH2:23][O:24][CH3:25])[CH2:9][C:8]1([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 73028854HCID 73028854, compound

Product 1

HCID 72991640HCID 72991640, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of hydrazone alcohol [29] (69 mg, 0.17 mmol) and MnO2 (300.8 mg, 3.46 mmol) in acetone (5 mL) was stirred at RT for 16 hr. The reaction mixture was filtered over a bed of Celite® and washed with acetone. The combined filtrates and washings were evaporated to give a residue, which was purified by column chromatography on silica using 30% ethyl acetate-hexane to provide the hydrazone aldehyde [30] (54.4 mg, 79%) and [α]D−532.6 (c 0.43, CH2Cl2).

Workup

  1. filtrationThe reaction mixture was filtered over a bed of Celite®
  2. washwashed with acetone
  3. customThe combined filtrates and washings were evaporated
  4. customto give a residue, which
  5. customwas purified by column chromatography on silica using 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-b056985c9b064ebcb89740d26e281de2
Source dataset
uspto-grants-2015_03
Patent number
US08969249B2

Reaction notes

Loading…