Isopropenyl acetate → HCID 178501043, compound

HRID 528701Notes

Reaction equation

HRID 528701 reaction equation
Cl[C:2](=[N:13][OH:14])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.C(O[C:19]([CH3:21])=[CH2:20])(=O)C.C(N(CC)CC)C>ClCCl>[CH3:12][O:11][C:9]([C@H:6]1[CH2:7][CH2:8][C@H:3]([C:2]2[CH:20]=[C:19]([CH3:21])[O:14][N:13]=2)[CH2:4][CH2:5]1)=[O:10]

Participants

5

Reactant 3

HCID 7916Isopropenyl acetateHCID 8471TriethylamineHCID 178501086HCID 178501086, compound

Product 1

HCID 178501043HCID 178501043, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-methyl 4-(chloro(hydroxyimino)methyl)cyclohexanecarboxylate (5.90 g, 26.9 mmol) and isopropenyl acetate (53.8 g, 537 mmol) in dichloromethane (134 ml) was added triethylamine (5.44 g, 53.7 mmol) at 0-5° C. The cooling bath was removed 15 minutes after completed addition, and the mixture was stirred for 20 h. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate (250 ml) and 0.1 M aqueous hydrochloric acid solution (200 ml). The organic layer was washed with one 100 ml-portion of 0.1 M aqueous hydrochloric acid solution. The combined aqueous layers were extracted with one 150 ml-portion of ethyl acetate. The combined organic layers were washed with one 200 ml-portion of 2 M sodium carbonate and one 100-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification with n-heptane/ethyl acetate as eluent gave the title compound (3.00 g, 50%) as off-white solid. MS m/e: 224 ([M+H]+)

Workup

  1. customThe cooling bath was removed 15 minutes
  2. additionaddition
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate (250 ml) and 0.1 M aqueous hydrochloric acid solution (200 ml)
  5. washThe organic layer was washed with one 100 ml-portion of 0.1 M aqueous hydrochloric acid solution
  6. extractionThe combined aqueous layers were extracted with one 150 ml-portion of ethyl acetate
  7. washThe combined organic layers were washed with one 200 ml-portion of 2 M sodium carbonate and one 100-ml portion of brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification with n-heptane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-d47950ba2ae84e68899523a3e414dc8e
Source dataset
uspto-grants-2016_05
Patent number
US09346824B2

Reaction notes

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