Malonic Acid → HCID 67527973, compound

HRID 1512161Notes

Reaction equation

HRID 1512161 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1>N1C=CC=CC=1>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([CH:11]=[CH:14][C:15]([OH:17])=[O:16])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehyde

Product 1

HCID 67527973HCID 67527973, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1,4-dioxa-spiro[4.5]decane-8-carbaldehyde (3.1 g, 18.4 mmol, prepared as in STEP B above), malonic acid (3.8 g, 36.5 mmol), piperidine (0.182 mL, 1.8 mmol) in pyridine (20 mL) was stirred at 70° C. under an argon atmosphere. After 3 h the resulting solution was concentrated. The residue obtained was partitioned between ethyl acetate and water. The layers were separated, and the ethyl acetate layer was washed successively with water and brine. The ethyl acetate layer was dried over sodium sulfate and was filtered, concentrated, and dried in vacuo to yield 3-(1,4-dioxa-spiro[4.5]dec-8-yl)-acrylic acid.

Workup

  1. concentrationAfter 3 h the resulting solution was concentrated
  2. customThe residue obtained
  3. customwas partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. washthe ethyl acetate layer was washed successively with water and brine
  6. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  7. filtrationwas filtered
  8. concentrationconcentrated
  9. customdried in vacuo

Sources & evidence

ORD record
ord-cf26a86306e6459fb59fecabbe1bde3d
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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