Ethyl Propionate → HCID 68453922, compound

HRID 2353590Notes

Reaction equation

HRID 2353590 reaction equation
[CH3:1][C:2]1([CH3:9])[C@@H:7]2[C@H:3]1[CH2:4][C:5](=[O:8])[CH2:6]2.[C:10](OCC)(=[O:13])[CH2:11][CH3:12]>C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:1][C:2]1([CH3:9])[CH:7]2[CH:3]1[CH2:4][C:5](=[O:8])[CH:6]2[C:10](=[O:13])[CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 7749Ethyl PropionateHCID 14138962HCID 14138962, compound

Product 1

HCID 68453922HCID 68453922, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1S,5R)-6,6-dimethyl-bicyclo[3.1.0]hexan-3-one (2.0 g, 16.1 mmol, step f above) in THF (20 mL) is treated with K. tert.-butylate (1.99 g, 17.7 mmol). The dark brown solution is stirred at rt for 30 min before ethyl propionate (18.5 mL, 161 mmol) is added. Stirring is continued at rt for 1 h. The mixture is diluted with 10% aq. citric acid and extracted with diethyl ether. The organic extract is washed with brine, dried over NaSO4 and the solvent is evaporated to leave rac-(1S,5R)-6,6-dimethyl-2-propionyl-bicyclo[3.1.0]hexan-3-one (2.35 g) as a brown oil. LC-MS: tR=0.99 min, [M+1]+=181.29, 1H NMR (CDCl3): δ 2.64 (dd, J=7.6, 20.0 Hz, 1H), 2.36-2.22 (m, 3H), 1.75 (d, J=7.6 Hz, 1H), 1.30-1.22 (m, 1H), 1.18 (t, J=7.6 Hz, 3H), 1.10 (s, 3H), 0.82 (s, 3H).

Workup

  1. additionis added
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over NaSO4
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-63e1a2e4f59647f3adf8e5944e45283a
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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