8-(3-(4-Chlorophenyl)-3-hydroxypropyn-1-yl)-1,4-dioxaspiro[4.5]decan-8-ol → 1-(4-Chlorophenyl)-3-(8-hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-2-propyn-1-one

HRID 1802521Notes

Reaction equation

HRID 1802521 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[C:9]#[C:10][C:11]2([OH:21])[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[C:9]#[C:10][C:11]2([OH:21])[CH2:20][CH2:19][C:14]3([O:15][CH2:16][CH2:17][O:18]3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 583993508-(3-(4-Chlorophenyl)-3-hydroxypropyn-1-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 583994351-(4-Chlorophenyl)-3-(8-hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-2-propyn-1-oneYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(3-(4-chlorophenyl)-3-hydroxypropyn-1-yl)-1,4-dioxaspiro[4.5]decan-8-ol (Reference Example 5) (7.70 g, 23.9 mmol) in dichloromethane (120 mL), manganese dioxide (10.4 g, 119 mmol) was added, and the obtained solution was stirred at room temperature for 18 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 (5.45 g, 17.0 mmol, 71%) as an 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-d1f6528c2f3941a88793f9f6614315a9
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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