Acetaldehyde → 4-Phenyl-3-butyn-2-ol

HRID 1033944Notes

Reaction equation

HRID 1033944 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[CH:20](=[O:22])[CH3:21]>C1COCC1.CCOCC>[C:1]1([C:7]#[C:8][CH:20]([OH:22])[CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 8058HexaneHCID 10821PhenylacetyleneHCID 178418339Butyllithium

Product 1

HCID 5829624-Phenyl-3-butyn-2-olYield 47%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phenylacetylene (5.5 mL; 50 mmol) was dissolved in THF (40 mL) and cooled to -78°. A 1.35M solution of n-butyllithium in hexane (37 mL; 50 mmol; 1.0 equiv.) was added dropwise and the resulting mixture was stirred at -78° for 1 h. Acetaldehyde (2.8 mL; 50 mmol; 1.0 equiv.) was added and the reaction mixture was allowed to warm overnight to room temperature. The mixture was diluted with ether (50 mL) and washed with water (3×25 mL). The organic solution was dried (MgSO4) and concentrated, and the crude product was distilled in vacuo, affording 3.4 g (47%) of 1f, bp 94° C./approximately 2 mm Hg. 1H nmr (300 MHz, CDCl3): 7.444-7.261 (5H, m); 4.762 (1H, q, J=5 96 Hz); 1.972 (1H, s); 1.557 (3H, d, J=6.58 Hz). IR (neat film, cm-1): 3400 (s); 1600 (w). FDMS (m/e): 146 (M+).

Workup

  1. temperaturecooled to -78°
  2. temperatureto warm overnight to room temperature
  3. washwashed with water (3×25 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. concentrationconcentrated
  6. distillationthe crude product was distilled in vacuo

Sources & evidence

ORD record
ord-7f411f13c6594d38a5a48f46a18d77e6
Source dataset
uspto-grants-1994_05
Patent number
US05312950

Reaction notes

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