Acetic Acid → HCID 57138079, compound

HRID 2255267Notes

Reaction equation

HRID 2255267 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]=1NC(C)C1C=CC=CC=1.[CH:22]([C:24]([CH3:26])=[O:25])=[CH2:23].C(O)(=[O:29])C>C1COCC1>[OH:25][C:24]1([CH3:26])[CH:4]2[C:3](=[O:29])[C@:2]([CH3:1])([C:11]3[CH:10]=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=3[CH2:5]2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6570Methyl vinyl ketoneHCID 19707369HCID 19707369, compound

Product 1

HCID 57138079HCID 57138079, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-methyl-2-(α-methylbenzylamino)-6-chloro-1,2-didehydrotetralin (79 g; 0.25 mol.) in 500 mL of THF was added methyl vinyl ketone (23 mL; 0.28 mol.). The solution was stirred at ambient temperature, under argon atmosphere, in the dark for 96 hours. Aqueous acetic acid (20%, 500 mL ) was added and the mixture stirred for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with saturated Na2CO3, and dried over Na2SO4. The solvent was removed under vacuum to afford 82 g of the subtitle compound as brown oil which was used without further purification.

Workup

  1. stirringthe mixture stirred for 2 hours
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated Na2CO3
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ba946ff8dd1b4a5f95b6ad02daf27439
Source dataset
uspto-grants-1993_08
Patent number
US05239075

Reaction notes

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