Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]- → HCID 178451083, compound

HRID 271347Notes

Reaction equation

HRID 271347 reaction equation
[C:1]([O:5][C:6]([CH:8]=[C:9]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pt].C(O)C>[C:1]([O:5][C:6]([CH2:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 59834904Cyclobutanecarboxylic acid, 3-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-HCID 178418361HCID 178418361, compound

Product 1

HCID 178451083HCID 178451083, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 2 g of 3-tert-butoxycarbonylmethylene-cyclobutanecarboxylic acid, 150 mL of ethanol, 0.5 g of 5% platinum on carbon, and 200 mL of ethanol was stirred under 1 atm of hydrogen for 48 h overnight, filtered, diluted with 20 mL of toluene and concentrated under reduced pressure. Drying under vacuum overnight gave 2 g of product, which was predominantly as a colorless oil: 1H NMR (400 MHz, CDCl3) 10.2 (br s, 1H), 3.0 (m, 1H), 2.3 (m, 1H), 2.38 (m, 4H), 2.0 (dd, 2H), 1.4 (s, 9).

Workup

  1. filtrationfiltered
  2. additiondiluted with 20 mL of toluene
  3. concentrationconcentrated under reduced pressure
  4. customDrying under vacuum overnight

Sources & evidence

ORD record
ord-95a0efb0825e4a77adb744b40e72c890
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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