HCID 58982097, compound → HCID 23072385, compound

HRID 1182476Notes

Reaction equation

HRID 1182476 reaction equation
[OH:1][CH:2]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10]>CC(C)=O.[O-2].[Mn+4].[O-2]>[CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[O:1]

Participants

4

Reactant 1

HCID 58982097HCID 58982097, compound

Product 1

HCID 23072385HCID 23072385, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 1-hydroxy-1-[(2-naphthyl)]-8-octanol 70 (715 mg, 2.63 mmol) in acetone (25 mL) was added manganese (IV) oxide (7.0 g, 81 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The mixture was filtered through a short pad of Celite and the solvents were removed in vacuo. The title compound 71 (361 mg, 51%) was isolated by column chromatography (4:6 ethyl acetate:hexane). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 1H), 8.11 (d, 1H), 8.00 (m, 3H), 7.64 (m, 2H), 4.32 (t, 1H), 3.15 (t, J=7.2 Hz, 2H), 1.67 (m, 2H), 1.40 (m, 2H), 1.32 (m, 8H).

Workup

  1. filtrationThe mixture was filtered through a short pad of Celite
  2. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-d19dc92527aa4d40981348a95cceec6f
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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