ethyl[5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-ylidene]ethanoate → ethyl[5,5-dimethylhexahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'-yl]acetate

HRID 1039971Notes

Reaction equation

HRID 1039971 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[C:6]1[CH2:13][CH:12]2[CH:8]([CH2:9][C:10]3([O:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][O:14]3)[CH2:11]2)[CH2:7]1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:7][CH:8]2[CH:12]([CH2:11][C:10]3([O:18][CH2:17][C:16]([CH3:20])([CH3:19])[CH2:15][O:14]3)[CH2:9]2)[CH2:13]1)[CH3:2]

Participants

4

Reactant 1

HCID 131730892ethyl[5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-ylidene]ethanoate

Product 1

HCID 86731803ethyl[5,5-dimethylhexahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'-yl]acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Step 2 (400 mg, 1.359 mmol) and 10% Pd—C-50% wet (85 mg, 0.799 mmol) in EtOAc (8.0 mL) was stirred 16 hrs at room temperature under a hydrogen atmosphere. The catalyst was then filtered off and the volatiles were removed under reduced pressure to give ethyl[5,5-dimethylhexahydro-1′H-spiro[1,3-dioxane-2,2′-pentalen]-5′-yl]acetate as a colorless oil. MS ESI: [M+Na]+ m/z 297.7.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-d71fb29d80c84b518ae86a734930f26a
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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