HCID 67296398, compound → HCID 67296414, compound

HRID 1802520Notes

Reaction equation

HRID 1802520 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:3]#[C:4][C:5]1([OH:15])[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1>ClCCl.[O-2].[O-2].[Mn+4]>[OH:15][C:5]1([C:4]#[C:3][C:2]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:1])[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 67296398HCID 67296398, compound

Product 1

HCID 67296414HCID 67296414, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(3-hydroxy-3-(4-methoxyphenyl)propyn-1-yl)-1,4-dioxaspiro[4.5]decan-8-ol (Reference Example 4) (7.10 g, 22.3 mmol) in dichloromethane (100 mL), manganese dioxide (9.69 g, 112 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, 17.2 mmol, 77%) 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-17b99dc4995448ecb04986cfa1c7c4bf
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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