Acetic Acid → HCID 18937576, compound

HRID 357647Notes

Reaction equation

HRID 357647 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][O:21][CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([N+:32]([O-:34])=[O:33])=[C:28]([CH:31]=1)[CH:29]=[O:30].C(O)(=O)C>O1CCCC1>[OH:30][CH:29]([C:28]1[CH:31]=[C:24]([O:23][CH2:22][O:21][CH3:20])[CH:25]=[CH:26][C:27]=1[N+:32]([O-:34])=[O:33])[C:15]#[C:14][C:13]([O:17][CH2:18][CH3:19])=[O:16]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 12182Ethyl propiolateHCID 11550252HCID 11550252, compoundHCID 178418339Butyllithium

Product 1

HCID 18937576HCID 18937576, compoundYield 135.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

1.5N butyllithium (14.9 ml, 22.4 mmole) was added under the argon atmosphere to a solution of diisopropylamine (3.3 ml, 23.8 mmole) in tetrahydrofuran (40 ml) at -78° C., and the mixture was stirred for 1.5 hours. Next, a solution of ethyl propiolate (2.7 ml, 26.8 mmole) in tetrahydrofuran (10 ml) and a solution of 5-methoxymethoxy-2-nitrobenzaldehyde (3.15 g, 14.9 mmole) in tetrahydrofuran (10 ml) were added in this sequence, and the reaction mixture was stirred at -78° C. for further 1 hour. After a solution of acetic acid (2.6 ml, 46.2 mmole) in tetrahydrofuran (10 ml) was added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, 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-(5-methoxymethoxy-2-nitrophenyl)-2-butynoate as an oil (6.26 g).

Workup

  1. stirringthe reaction mixture was stirred at -78° C. for further 1 hour
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with dilute hydrochloric acid
  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-828178363a9540b4bb1cd35bcd346db3
Source dataset
uspto-grants-1998_11
Patent number
US05840895

Reaction notes

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