Methyl 2-(1,4-dioxaspiro[4.5]decan-8-ylidene)acetate → Methyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate

HRID 1028199

Reaction equation

HRID 1028199 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[C:5]1[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][CH2:6]1.[H][H]>[C].[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]1[CH2:14][CH2:13][C:8]2([O:9][CH2:10][CH2:11][O:12]2)[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 11063747Methyl 2-(1,4-dioxaspiro[4.5]decan-8-ylidene)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 20711792Methyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetateYield 75.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

An ethanol (50 mL) suspension of (1,4-dioxa-spiro[4.5]dec-8-ylidene)-acetic acid methyl ester (6.57 g) obtained in Example (1a) and palladium carbon (10% by weight) was hydrogen-reduced at room temperature for 24 hours. The reaction mixture was filtered and concentrated. The residue was purified by chromatography (hexane/ethyl acetate=5:1) to obtain the title compound (4.99 g, 75%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-b79eea263fae4da280a7ec3f90fa45f7
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Linked notes

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