p-Toluenesulfonic acid → 5-t-Butyl-2-(4-ethynylphenyl)-1,3-oxathiane

HRID 346255

Reaction equation

HRID 346255 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[CH:3]([CH2:6][SH:7])[CH2:4][OH:5].[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)#[CH:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:2]([CH:3]1[CH2:4][O:5][CH:16]([C:15]2[CH:18]=[CH:19][C:12]([C:10]#[CH:11])=[CH:13][CH:14]=2)[S:7][CH2:6]1)([CH3:9])([CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 27716454-EthynylbenzaldehydeHCID 19990620HCID 19990620, compound

Product 1

HCID 199906265-t-Butyl-2-(4-ethynylphenyl)-1,3-oxathiane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3,3-dimethyl-2-mercaptomethylbutan-1-ol (1.46 g), 4-ethynylbenzaldehyde (1.30 g) (W.B. Austin et al. J. Org. Chem., 1981, 46. 2280) and para-toluenesulphonic acid (10 mg) in benzene (50 ml) was heated to reflux overnight under Dean and Stark conditions. The resulting solution was evaporated under reduced pressure and the residue was purified on silica. Elution with 4:1 hexane: dichloromethane gave 5-t-butyl-2-(4-ethynylphenyl)-1,3-oxathiane as a mixture of isomers.

Workup

  1. temperatureto reflux overnight under Dean and Stark conditions
  2. customThe resulting solution was evaporated under reduced pressure
  3. customthe residue was purified on silica
  4. washElution with 4:1 hexane

Sources & evidence

ORD record
ord-c9cf745b0adf40639ca7aee192e3a0dc
Source dataset
uspto-grants-1991_10
Patent number
US05061726

Linked notes

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