Acetic Acid → HCID 59736092, compound

HRID 133812

Reaction equation

HRID 133812 reaction equation
CC(C)([O-:4])C.[K+].[N+:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[C-:8].[CH2:15]1[C:24](=O)[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1.C(O)(=O)C>O1CCCC1>[C:16]1(=[C:9](/[NH:7][CH:8]=[O:4])\[C:10]([O:12][CH2:13][CH3:14])=[O:11])\[CH2:15][CH2:24][CH2:23][C:22]2[C:17]\1=[CH:18][CH:19]=[CH:20][CH:21]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 682662-TetraloneHCID 533707Ethyl isocyanoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 59736092HCID 59736092, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of potassium t-butoxide (4.7 g, 42.0 mmol) in 30 mL tetrahydrofuran at 0° C. is added ethyl isocyanoacetate (4.53 g, 40.0 mmol). This is stirred for 30 mins whereupon a solution of β-tetralone (5.88 g, 40.0 mmol) in tetrahydrofuran (20 mL) is added dropwise. The reaction mixture is allowed to warm to room temperature and stirred for 3 hours. The reaction mixture is then recooled in an ice bath and to this is added acetic acid (2.5 g, 41.6 mmol), allowed to warm to room temperature and stirred for an additional 30 mins. The solvent is removed in-vacuo and the residue partitioned between water and ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered, evaporated and crystallized from cyclohexane to give 4.67 g of a white solid (contains some E-isomer), MS: m/z 260.2 (M+1).

Workup

  1. additionis added dropwise
  2. customThe reaction mixture is then recooled in an ice bath
  3. temperatureto warm to room temperature
  4. stirringstirred for an additional 30 mins
  5. customThe solvent is removed in-vacuo
  6. customthe residue partitioned between water and ethyl acetate
  7. washThe organic layer is washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customcrystallized from cyclohexane

Sources & evidence

ORD record
ord-a8160e7125b049a2b8a174406f9a3c0f
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Linked notes

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