Toluene → Ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate

HRID 2261729Notes

Reaction equation

HRID 2261729 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 22285400Ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate

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 min. 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-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-c3d626ffd6814df7a867f35235bc9b8c
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…