HCID 18340695, compound → 1,1-Dimethylethyl 4-(ethoxycarbonyl)cyclohexaneacetate

HRID 1913212Notes

Reaction equation

HRID 1913212 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH:7]=[C:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13]1)([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 18340695HCID 18340695, compound

Product 1

HCID 666136151,1-Dimethylethyl 4-(ethoxycarbonyl)cyclohexaneacetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL round-bottom flask was charged ethyl 4-(2-tert-butoxy-2-oxoethylidene)cyclohexanecarboxylate (Int-4a, 5.38 g, 19.90 mmol) followed by EtOAc (100 mL). The flask was flushed with argon and then 5% palladium on carbon was added. The flask was sealed and degassed under vacuum. H2 (g) was added in a balloon and the reaction was allowed to stir 18 hours under hydrogen atmosphere. After 18 hours, the reaction mixture was filtered through celite. The solvent was removed in vacuo and the resulting oil was taken on without further purification.

Workup

  1. customThe flask was flushed with argon
  2. addition5% palladium on carbon was added
  3. customThe flask was sealed
  4. customdegassed under vacuum
  5. additionH2 (g) was added in a balloon
  6. waitAfter 18 hours
  7. filtrationthe reaction mixture was filtered through celite
  8. customThe solvent was removed in vacuo
  9. customthe resulting oil was taken on without further purification

Sources & evidence

ORD record
ord-6fa096afaeb1418ea822e43253b338f9
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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