2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thiazole → 2-(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiazole

HRID 1016041Notes

Reaction equation

HRID 1016041 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>CO.[Pd]>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 595561422-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thiazole

Product 1

HCID 595560502-(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiazoleYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Parr hydrogenation bottle was added 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3-thiazole (0.22 g, 0.99 mmol), dissolved in methanol (15 mL), followed by the addition of 10% Pd/C (0.08 g). This mixture was hydrogenated at 50 psi overnight. After the catalyst was filtered and washed with methanol, the filtrate was concentrated in vacuo to give 0.21 g of 2-(1,4-dioxaspiro[4.5]dec-8-yl)-1,3-thiazole in 95% yield. MS (EI) calcd: (M+1)+=226.1; found: 225.9.

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationAfter the catalyst was filtered
  3. washwashed with methanol
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5ef20991c93540bbbc7cb238b31c67c8
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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