Acetic Acid → HCID 18937697, compound

HRID 357651Notes

Reaction equation

HRID 357651 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15].[CH3:20][C:21]1[C:28]([CH3:29])=[CH:27][C:24]([CH:25]=[O:26])=[C:23]([N+:30]([O-:32])=[O:31])[CH:22]=1.C(O)(=O)C>O1CCCC1.O>[OH:26][CH:25]([C:24]1[CH:27]=[C:28]([CH3:29])[C:21]([CH3:20])=[CH:22][C:23]=1[N+:30]([O-:32])=[O:31])[C:15]#[C:14][C:13]([O:17][CH2:18][CH3:19])=[O:16]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 12182Ethyl propiolateHCID 21476134HCID 21476134, compoundHCID 178418339Butyllithium

Product 1

HCID 18937697HCID 18937697, compoundYield 108.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

1.5N butyllithium (15.8 ml, 24.88 mmole) was added under the argon atmosphere to a solution of diisopropylamine (3.66 ml, 26.1 mmole) in tetrahydrofuran (50 ml) at -78° C., and the mixture was stirred for 30 minutes. To the reaction mixture were next added a solution of ethyl propiolate (2.20 ml, 21.71 mmole) in tetrahydrofuran (10 ml) and a solution of 4, 5-dimethyl-2-nitrobenzaldehyde (2.60 g, 14.51 mmole) in tetrahydrofuran (20 ml) in this sequence, and the reaction mixture was stirred at -78° C. for further 1.5 hours. After a solution of acetic acid (3.2 ml, 53.3 mmole) in tetrahydrofuran (10 ml) followed by water were added, the reaction mixture was extracted with ethyl acetate (300 ml). The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous saline in this sequence. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure to give ethyl 4-hydroxy-4-(4,5-dimethyl-2-nitrophenyl)-2-butynoate as an oil (4.363 g).

Workup

  1. additionwere added
  2. extractionthe reaction mixture was extracted with ethyl acetate (300 ml)
  3. washThe organic layer was washed with dilute hydrochloric acid, water
  4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b9d8f31854dc4ffcabe6b269951772f8
Source dataset
uspto-grants-1998_11
Patent number
US05840895

Reaction notes

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