Dimethylformamide → 5-tert-Butyl-2-(4-ethynylphenyl)-1,3-dithiane

HRID 1441052Notes

Reaction equation

HRID 1441052 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[CH:2].[C:11]([CH:15]([CH2:18][SH:19])[CH2:16][SH:17])([CH3:14])([CH3:13])[CH3:12].CN(C)C=O.S(OC)(OC)(=O)=O>C(Cl)Cl.C(N(CC)CC)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[S:19][CH2:18][CH:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:16][S:17]2)=[CH:5][CH:4]=1)#[CH:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 27716454-EthynylbenzaldehydeHCID 149804272-tert-Butylpropane-1,3-dithiol

Product 1

HCID 224210215-tert-Butyl-2-(4-ethynylphenyl)-1,3-dithiane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-ethynylbenzaldehyde (131 mg., 1.00 mmol.), 2-t-butylpropane-1,3-dithiol (206 mg., 1.25 mmole) (E. L. Eliel and R. O. Hutchins (J. Amer. Chem. Soc. 1969, 91, 2703)) and the adduct of N,N-dimethylformamide and dimethyl sulphate (300 mg., 1.50 mmole) diluted with methylene chloride (2.0 ml.) was maintained at 23° for 48 hours. After cooling to 0°, triethylamine (0.2 ml) was added, and the solution was washed with water (3×2 ml.) which was again extracted with methylene chloride. The combined organic layers were dried (anhydrous magnesium sulphate) and evaporated to give a residue (320 mg.) which was recrystallized from hexane (2.5 ml.) to give 2-(4-ethynylphenyl)-5-t-butyl-1,3-dithiane, m.p. 149°, (120 mg , 43%)

Workup

  1. temperaturewas maintained at 23° for 48 hours
  2. temperatureAfter cooling to 0°
  3. washthe solution was washed with water (3×2 ml.) which
  4. extractionwas again extracted with methylene chloride
  5. dry with materialThe combined organic layers were dried (anhydrous magnesium sulphate)
  6. customevaporated
  7. customto give a residue (320 mg.) which
  8. customwas recrystallized from hexane (2.5 ml.)

Sources & evidence

ORD record
ord-217afb076f1045989fd0b1c99ead4ca8
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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