Tetrahydrofuran → HCID 18386053, compound

HRID 2298303Notes

Reaction equation

HRID 2298303 reaction equation
[C:1]([C:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[CH2:9]([Li])[CH2:10][CH2:11]C.CC1C=CC([CH:19]=[S:20])=CC=1.[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>CCCCCC>[OH:26][CH:25]([C:24]1[CH:23]=[CH:27][C:11]([S:20][CH3:19])=[CH:10][CH:9]=1)[C:2]#[C:1][C:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 870741-EthynylcyclopentanolHCID 181775354-MethylthiobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 18386053HCID 18386053, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 1-ethynyl-cyclopentan-1-ol (2.0 g) in 15 ml dry THF at −78° C. under argon, was added 18 ml of 2.5 M butyllithium in hexane dropwise over 20 minutes. The reaction solution was stirred for another 20 minutes, which was followed by the addition of 4-methylthiobenzaldehyde (2.7 g) dropwlse. After stirring for another 2 hours, the reaction was quenched by adding 20 ml of dilute aqueous HCl. The reaction solvent was removed in vacuo, and the resulting aqueous solution was extracted with dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure and the resulting residue was purified by column chromatography (hexane/ethylacetate=1:1) to yield 3.48 g of 1-[3-hydroxy-3-{4-(methylthio)phenyl}-prop-1-ynyl]-cyclopentanol as a solid. mp: 118-120° C. NMR: δ0.73 (m, 4H), 1.87 (m, 4H), 2.16 (s, 1H), 2.48 (s, 3H), 2.55 (s, 1H), 5.43 (d, J=5.7 Hz, 1H), 7.24(d, J=8.4 Hz, 2H), 7.42 (d, J=8.4 Hz, 2H).

Workup

  1. stirringAfter stirring for another 2 hours
  2. customthe reaction was quenched
  3. additionby adding 20 ml of dilute aqueous HCl
  4. customThe reaction solvent was removed in vacuo
  5. extractionthe resulting aqueous solution was extracted with dichloromethane (30 ml×3)
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe resulting residue was purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-f88e5c06047d4af6a0cde1298120822b
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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