HCID 58399442, compound → HCID 58399458, compound

HRID 1802517Notes

Reaction equation

HRID 1802517 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[C:3]#[C:4][C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>ClCCl.[O-2].[O-2].[Mn+4]>[OH:11][C:5]1([C:4]#[C:3][C:2]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[O:1])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 58399442HCID 58399442, compound

Product 1

HCID 58399458HCID 58399458, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-hydroxy-3-(p-tolyl)propyn-1-yl)cyclohexanol (Reference Example 2) (593 mg, 2.42 mmol) in dichloromethane (20 mL), manganese dioxide (1.15 g, 13.2 mmol) was added, and the obtained solution was stirred at room temperature for 5 hours. The reaction solution was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (534 mg, 2.20 mmol, 91%) as a light yellow oily product.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-80491d0c76834b6fa508859337cee42f
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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