8-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]dec-7-ene → 8-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]decane

HRID 585634Notes

Reaction equation

HRID 585634 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:24][CH2:23][C:18]2([O:22][CH2:21][CH2:20][O:19]2)[CH2:17][CH:16]=1>[Pd]>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:24][CH2:23][C:18]2([O:19][CH2:20][CH2:21][O:22]2)[CH2:17][CH2:16]1

Participants

3

Reactant 1

HCID 121351688-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 121351698-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]decaneYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

8-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]dec-7-ene (0.950 g, 2.83 mmol) and palladium (200 mg, 10% on carbon) were stirred under an atmosphere of hydrogen for 15 hr. The mixture was then filtered through a plug of Celite, washing with ethyl acetate. The filtrate was then evaporated to dryness, affording the desired product (0.955 g, 100%) as a colourless oil. δH (CDCl3) 1.67-1.87 (8H, m), 2.90-2.99 (1H, m), 3.46 (3H, s), 3.48 (3H, s), 3.97 (4H, s), 5.12 (2H, s), 5.18 (2H, s), 6.65 (1H, dd), 6.78 (1H, d), 7.12 (1H, d).

Workup

  1. filtrationThe mixture was then filtered through a plug of Celite
  2. washwashing with ethyl acetate
  3. customThe filtrate was then evaporated to dryness

Sources & evidence

ORD record
ord-ba494b28258e42559f10cc2594fedecd
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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