HCID 54437313, compound → HCID 54058363, compound

HRID 1755782Notes

Reaction equation

HRID 1755782 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@@H:10]([S:19][CH2:20][C:21]1([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:23][CH2:22]1)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=1>CCOC(C)=O.O=[Mn]=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@@H:10]([S:19][CH2:20][C:21]1([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:22][CH2:23]1)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=1

Participants

4

Reactant 1

HCID 54437313HCID 54437313, compound

Product 1

HCID 54058363HCID 54058363, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the benzylic alcohol of Step 7 (1.176 g, 2.54 mmol) and activated MnO2 (4.6 g, 20 equiv.) in 25 mL of EtOAc was stirred at room temperature for 4 hr. Another batch of MnO2 (1.1 g) was added and the mixture was stirred 20 min. It was filtered through celite to afford 1.014 g (87%) of the title aldehyde.

Workup

  1. stirringthe mixture was stirred 20 min
  2. filtrationIt was filtered through celite

Sources & evidence

ORD record
ord-9240be5958ea42f69bbec73d6080c8ca
Source dataset
uspto-grants-1995_08
Patent number
US05438141

Reaction notes

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