D-Psicose → Methyl 4-(1,4-dioxaspiro[4.5]dec-8-yl)benzoate

HRID 1443420Notes

Reaction equation

HRID 1443420 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd].CCOC(C)=O.CO>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 22730331Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoate

Product 1

HCID 59881361Methyl 4-(1,4-dioxaspiro[4.5]dec-8-yl)benzoateYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoate (514 mg, 1.87 mmol) and 10% Pd/C (127 mg) in 15 mL of 1:2 v/v EtOAc/CH3OH was shaken for 6.5 h under 45 Psi of H2 using a Parr shaker. Catalyst was filtered off through a cake of Celite and washed with copious of EtOAc. The filtrate was concentrated to give 480 mg of the title compound.

Workup

  1. filtrationCatalyst was filtered off through a cake of Celite
  2. washwashed with copious of EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7ca351f5bd5a4bc9849f78831f843156
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

Loading…