Water → Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester

HRID 1960035Notes

Reaction equation

HRID 1960035 reaction equation
[H-].[Na+].[CH2:3]1[O:13][C:6]2([CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]2)[O:5][CH2:4]1.[OH2:14].[CH2:15]1[CH2:19][O:18][CH2:17][CH2:16]1>>[CH2:17]([O:18][C:19]([CH:15]=[C:9]1[CH2:10][CH2:11][C:6]2([O:13][CH2:3][CH2:4][O:5]2)[CH2:7][CH2:8]1)=[O:14])[CH3:16]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 373318Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester

Procedure

Triethylphosphonoacetate (146 mL, 0.74 mol) is added to a suspension of NaH (60% in oil, 29.5 g, 0.74 mol) in THF (2500 mL) at 0-5° C., and the mixture is stirred for 30 min at the same temperature. To the mixture is added dropwise 1,4-cyclohexanedione monoethylene acetal (100 g, 0.64 mol) in THF (700 mL) at 0-5° C. and stirring is continued for 1 hour at the same temperature. After addition of H2O (1500 mL), the mixture is extracted with EtOAc (3000 mL). The water layer is extracted with EtOAc (1500 mL×2) and combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford 8-ethoxycarbonylmethylidene-1,4-dioxaspiro[4.5]decane (172.9 g) as a colorless oil. The crude product is used without further purification.

Workup

  1. stirringstirring
  2. waitis continued for 1 hour at the same temperature
  3. extractionthe mixture is extracted with EtOAc (3000 mL)
  4. extractionThe water layer is extracted with EtOAc (1500 mL×2)
  5. washis washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e207a76e73314655b9798ce36e9bb657
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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