Toluene → HCID 22285400, compound

HRID 1689751

Reaction equation

HRID 1689751 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5]C=CC=1.[H-].[Na+].[S:10]1[CH2:15][CH2:14][CH2:13][S:12][CH:11]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].BrCC1CC1>CN(C=O)C>[CH2:19]([O:18][C:16]([C:11]1([CH2:7][CH:1]2[CH2:6][CH2:5]2)[S:12][CH2:13][CH2:14][CH2:15][S:10]1)=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 88552Ethyl 1,3-dithiane-2-carboxylate

Product 1

HCID 22285400HCID 22285400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flamed dried flask is added dry toluene (80 mL) and sodium hydride (60%, 33.5 mmol, 1.34 g). The reaction is cooled in a ice bath and a solution of ethyl 1,3 dithiane carboxylate (52 mmol, 10 g) and bromomethyl cyclopropane (62.4 mmol, 8.42 g) in DMF (24 mL) are added dropwise over 10 minutes. The ice bath is removed and the reaction is stirred for 18 h. Water is added (50 mL) and the organic layer is separated. The organic layer is washed with brine, dried (Na2SO4), and concentrated to a yellow oil (12 g, 92%). LC-ES/MS: 247.0 (M+1).

Workup

  1. customTo a flamed dried flask
  2. temperatureThe reaction is cooled in a ice bath
  3. customThe ice bath is removed
  4. additionWater is added (50 mL)
  5. customthe organic layer is separated
  6. washThe organic layer is washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to a yellow oil (12 g, 92%)

Sources & evidence

ORD record
ord-2b7089650b25413781be88d029022323
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Linked notes

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