1-Ethynylcyclohexanol → HCID 18385851, compound

HRID 2298308Notes

Reaction equation

HRID 2298308 reaction equation
[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[CH2:10]([Li])[CH2:11][CH2:12]C.CC1C=CC([CH:20]=[S:21])=CC=1.[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>CCCCCC>[OH:27][CH:26]([C:25]1[CH:24]=[CH:28][C:12]([S:21][CH3:20])=[CH:11][CH:10]=1)[C:2]#[C:1][C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 65251-EthynylcyclohexanolHCID 8028TetrahydrofuranHCID 181775354-MethylthiobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 18385851HCID 18385851, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 1-ethynyl-cyclohexan-1-ol (3.2 g) in 80 ml dry THF at −78° C. and under argon, was added dropwise 35 ml of 2.5 M butyllithium in hexane over 10 minutes. The reaction solution was stirred for another 20 minutes, which was followed by the dropwise addition of 4-methylthiobenzaldehyde (3.2 ml). After stirred for another 2 hours, the reaction was quenched by adding dilute aqueous HCl. The reaction solvent was removed in vacuo, and the resulting aqueous solution was extracted with dichloromethane. The organic layer was concentrated under reduced pressure and the resulting residue was purified by column chromatography (hexane/ethylacetate) to yield 4.67 g of 1-[3-hydroxy-{4-(methylthio)phenyl}-prop-1-ynyl]-cyclohexanol. NMR: δ1.45 (m, 6H), 1.70 (m, 2H), 1.90 (m, 2H), 2.17 (d, 1H), 2.49 (s, 3H), 3.57 (s, 1H), 5.48 (d, J=6.0 Hz 1H), 7.26 (d, J=8.4 Hz, 2H), 7.46 (d, J=8.4 Hz, 2H). IR (cm−1): 3343, 2934, 1445, 1091.

Workup

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

Sources & evidence

ORD record
ord-0d5a49c36bc84317b940baad993b8229
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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