Sodium hydride → Ethyl 2-(4-chlorobutyl)-1,3-dithiane-2-carboxylate

HRID 1803199Notes

Reaction equation

HRID 1803199 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:13][CH2:14][CH2:15][CH2:16][Cl:17].[H-].[Na+]>CN(C=O)C>[Cl:17][CH2:16][CH2:15][CH2:14][CH2:13][C:2]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:3][CH2:4][CH2:5][CH2:6][S:1]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 88552Ethyl 1,3-dithiane-2-carboxylate

Product 1

HCID 86649922Ethyl 2-(4-chlorobutyl)-1,3-dithiane-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step AS (1): To a solution of ethyl 1,3-dithiane-2-carboxylate (500 mg, 2.60 mmol) and 1-bromo-4-chlorobutane (1337 mg, 7.80 mmol) in DMF (10 mL) was added 60% NaH (dispersion in mineral oil, 125 mg, 3.12 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was quenched with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (3×100 mL) and concentrated in vacuo. The residue was purified using silica gel column chromatography (10% EtOAc/hexanes) to give ethyl 2-(4-chlorobutyl)-1,3-dithiane-2-carboxylate (550 mg, 75% yield). LC-MS (M+H)+ 283.0.

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with water (3×100 mL)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-568050fc6aea4e24a1d51e38041c9682
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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