Acetyl chloride → HCID 21964350, compound

HRID 270213Notes

Reaction equation

HRID 270213 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[S:13][CH2:12][CH2:11][CH2:10][S:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[C:19](Cl)(=[O:21])[CH3:20]>C1COCC1>[C:19]([C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[S:9][CH2:10][CH2:11][CH2:12][S:13]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11817100HCID 11817100, compoundHCID 178418339Butyllithium

Product 1

HCID 21964350HCID 21964350, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The crude 2-(3-chlorophenyl)-1,3-dithiane is dissolved in anhydrous THF (400 mL). After chilling to −78° C., a solution of n-butyl lithium (2.5 Molar, 42 mL) is added slowly by syringe. The solution is stirred for 30 min at −78° C., followed by the addition of acetyl chloride. The mixture is warmed to room temperature, quenched by the addition of a saturated aqueous solution of NH4Cl, washed with water, brine, and dried (Na2SO4). After removing the dessicant, the filtrate was concentrated in vacuo to provide the desired product.

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. customquenched by the addition of a saturated aqueous solution of NH4Cl
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customAfter removing the dessicant
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-705a071fa60642c0bf2a7fa1aa4434ba
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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