3-Ethyl-1-pentyn-3-ol → HCID 18386011, compound

HRID 2298298Notes

Reaction equation

HRID 2298298 reaction equation
[CH2:1]([C:3]([OH:8])([CH2:6][CH3:7])[C:4]#[CH:5])[CH3:2].C[Li].[CH3:11][S:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1>C1COCC1.CCCCCC>[CH2:4]([C:3]([OH:8])([CH2:6][CH3:7])[C:1]#[C:2][CH:17]([C:16]1[CH:19]=[CH:20][C:13]([S:12][CH3:11])=[CH:14][CH:15]=1)[OH:18])[CH3:5]

Participants

6

Reactant 3

HCID 226983-Ethyl-1-pentyn-3-olHCID 769854-(Methylthio)benzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 18386011HCID 18386011, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 3-ethyl-1-pentyn-3-ol (7.7 ml) in 300 ml anhydrous THF, was added dropwise 100 ml of 1.4 M methyllithium in hexane at −78° C. under argon. The mixture was further stirred for 30 minutes, followed by dropwise addition of 4-(methylthio)benzaldehyde (9.3 ml). The reaction mixture was stirred for another 12 hours, during which the cold bath was removed such that the reaction temperature reached room temperature slowly. Then the reaction was quenched by adding dilute aqueous HCl. The solvent was removed in vacuo and the resulting residue was extracted with brine and dichloromethane (150 ml×3). The organic layer was concentrated under reduced pressure and the resulting crude product was purified by recrystallization from hexane and ethylacetate (4:1) to give 11.8 g of 4-ethyl-1-{4-(methylthio)phenyl}-2-hexyn-1,4-diol as a low-melting solid. mp: 64-65° C. NMR: δ1.04 (t, J=7.5 Hz, 6H), 1.70 (q, J=7.5 Hz, 4H), 2.49 (s, 3H), 5.47 (s, 1H), 7.26 (d, J=8.4 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H). IR (cm−1): 3368, 2970, 2207, 1637, 1589, 1262, 1093.

Workup

  1. stirringThe reaction mixture was stirred for another 12 hours, during which the cold bath
  2. customwas removed such that the reaction temperature
  3. customreached room temperature
  4. customThen the reaction was quenched
  5. additionby adding dilute aqueous HCl
  6. customThe solvent was removed in vacuo
  7. extractionthe resulting residue was extracted with brine and dichloromethane (150 ml×3)
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. customthe resulting crude product was purified by recrystallization from hexane and ethylacetate (4:1)

Sources & evidence

ORD record
ord-4abfed25eba0481ab7134d5c9df7f2b5
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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