Sodium Chloride → 2-{1-(4-Phenoxyphenyl)propan-1-ylidene}-1,3-dithiane

HRID 2372426

Reaction equation

HRID 2372426 reaction equation
C(OP([CH:9]1[S:14][CH2:13][CH2:12][CH2:11][S:10]1)(OCC)=O)C.CCCCCC.C([Li])CCC.[CH:26]1[CH:31]=[CH:30][C:29]([C:32]([CH2:34][CH2:35][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=O)=[CH:28][CH:27]=1.[Cl-].[Na+]>O1CCCC1>[O:36]([C:35]1[CH:27]=[CH:28][C:29]([C:30](=[C:9]2[S:10][CH2:11][CH2:12][CH2:13][S:14]2)[CH2:31][CH3:26])=[CH:32][CH:34]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 38763553-Phenoxy-1-phenylpropan-1-oneHCID 10869064Diethyl (1,3-Dithian-2-yl)phosphonateHCID 178418339Butyllithium

Product 1

HCID 146740592-{1-(4-Phenoxyphenyl)propan-1-ylidene}-1,3-dithianeYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Diethoxyphosphoryl-1,3-dithiane, 4.18 g, was dissolved in 40 ml of tetrahydrofuran and 10.5 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added to the solution in an argon flow at -65° C. The mixture was stirred at the same temperature for an hour. Then, a solution of 36.2 g of 4-phenoxypropiophenone in 15 ml of tetrahydrofuran was dropwise added to the mixture at the same temperature. The reaction mixture was gradually warmed to room temperature overnight. This suspension was poured onto saturated sodium chloride aqueous solution followed by extraction with chloroform. After drying the chloroform phase over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1) to give 4.15 g of the product.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialAfter drying the chloroform phase over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1)

Sources & evidence

ORD record
ord-b15c063df7fe42a486b81c6326eca2d4
Source dataset
uspto-grants-1992_03
Patent number
US05098928

Linked notes

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