2-Methyl-1,3-dithiane → HCID 19862733, compound

HRID 1721964

Reaction equation

HRID 1721964 reaction equation
C([Li])CCC.[CH3:6][CH:7]1[S:12][CH2:11][CH2:10][CH2:9][S:8]1.Br[CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>C1COCC1>[CH3:6][C:7]1([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[S:12][CH2:11][CH2:10][CH2:9][S:8]1

Participants

5

Reactant 3

HCID 223292-Methyl-1,3-dithianeHCID 19862698HCID 19862698, compoundHCID 178418339Butyllithium

Product 1

HCID 19862733HCID 19862733, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.5M in hexane, 12 ml) was added over 5 min to a stirred solution of 2-methyl-1,3-dithiane (2.4 g) in dry THF (30 ml) at 70° under nitrogen. The yellow solution was then stirred at -30° to -20° for 2 h, cooled to -78° and treated with a solution of the product of stage (iii) (6.1 g) in THF (25 ml). The solution was stirred at room temperature overnight, the solvent was evaporated and the residue was purified by FCC (hexane→System D 9:1) to give the title compound as a pale yellow oil (3.2 g) T.l.c. (System D 9:1) Rf 0.18.

Workup

  1. temperaturecooled to -78°
  2. stirringThe solution was stirred at room temperature overnight
  3. customthe solvent was evaporated
  4. customthe residue was purified by FCC (hexane→System D 9:1)

Sources & evidence

ORD record
ord-6c496853f4524094953f62927c492981
Source dataset
uspto-grants-1989_08
Patent number
US04853381

Linked notes

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