Sodium Chloride → 2-[(4-Chlorophenyl)cyclopropylmethylene]-1,3-dithiane

HRID 1383218

Reaction equation

HRID 1383218 reaction equation
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.C([Li])CCC.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH:25]2[CH2:27][CH2:26]2)=O)=[CH:19][CH:18]=1.[Cl-].[Na+]>O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH:25]2[CH2:26][CH2:27]2)=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 811484-Chlorophenyl cyclopropyl ketoneHCID 834132-Trimethylsilyl-1,3-dithianeHCID 178418339Butyllithium

Product 1

HCID 539201222-[(4-Chlorophenyl)cyclopropylmethylene]-1,3-dithianeYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 16.0 grams (0.083 mole) of 2-trimethylsilyl-1,3-dithiane in 80 mL of tetrahydrofuran was cooled to 0° C., and 39 mL (0.083 mole) of n-butyllithium (2.1M in hexane) was added. The reaction mixture was stirred for 15 minutes, and 15.0 grams (0.083 mole) of cyclopropyl (4-chlorophenyl) ketone in 40 mL of tetrahydrofuran was added via syringe during a five minute period. Upon completion of addition, the reaction mixture was stirred at 0° C. for 15 minutes and then was allowed to warm for 30 minutes. The reaction mixture was stirred with 100 mL of an aqueous solution saturated with sodium chloride, and then the two phases were separated. The aqueous phase was extracted with one portion of diethyl ether. The ether extract was combined with the organic phase, and this mixture was dried with magnesium sulfate and filtered through a pad of silica gel. The filtrate was concentrated under reduced pressure, yielding 24.0 grams of 2-[(4-chlorophenyl)cyclopropylmethylene]-1,3-dithiane as a solid, m.p. 91°-95° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred at 0° C. for 15 minutes
  3. temperatureto warm for 30 minutes
  4. customthe two phases were separated
  5. extractionThe aqueous phase was extracted with one portion of diethyl ether
  6. extractionThe ether extract
  7. dry with materialthis mixture was dried with magnesium sulfate
  8. filtrationfiltered through a pad of silica gel
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe022474c79e42d29faabc3d1674c824
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Linked notes

Loading…