Water → HCID 53878501, compound

HRID 727131Notes

Reaction equation

HRID 727131 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:14][CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10].Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O>CN(C)C=O>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[O:16][CH2:15][CH2:14][C:11]([C:12]#[N:13])([C:6]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=1)[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 156708072-(3-Cyano-3-(3,4-dichlorophenyl)propyl)oxytetrahydropyran

Product 1

HCID 53878501HCID 53878501, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.6 g of 60% NaH are added in small portions to a solution of 36 g of the above 3,4-dichloro-α-[(2-tetrahydropyranyloxy)ethyl]benzeneacetonitrile (prepared according to PREPARATION II (a)) in 100 ml of dimethylformamide. The reaction mixture is stirred for 3 hours at room temperature and cooled to 0° C. and 22.4 g of ethyl 4-bromobutyrate in 40 ml of dimethylformamide are then added. The reaction mixture is stirred for 3 hours at room temperature, poured into water and extracted with ether and the extract is washed with a saturated solution of NaCl, dried over Na2SO4 and concentrated under vacuum. The residue obtained is purified by chromatography on silica gel using toluene as the eluent to give 24 g of the expected product.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture is stirred for 3 hours at room temperature
  3. extractionextracted with ether
  4. washthe extract is washed with a saturated solution of NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b96a781b085c497b84af3d61e7bef598
Source dataset
uspto-grants-1998_01
Patent number
US05712288

Reaction notes

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