Pentane → HCID 19066418, compound

HRID 481434Notes

Reaction equation

HRID 481434 reaction equation
[H-].[Na+].[CH3:3]CCCC.[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]([CH:27]=[CH2:28])[CH2:17][NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=[CH:13][C:14]=1[Cl:15].CCCCCC.CCOC(C)=O>CCCCCC.C1COCC1>[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]([CH:27]=[CH2:28])[CH2:17][N:18]([CH3:3])[C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

7

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 19066417HCID 19066417, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 19066418HCID 19066418, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
23 °C

Procedure

Wash a suspension of NaH (312 mg of 60% in mineral oil, 7.81 mmol, 1.25 eq) in hexane with dry pentane (2×100 mL), suspend in dry THF (30 mL) and treat with the product of step 7 (2.0 g, 6.25 mmol) at 23° C. Stir the resulting yellow suspension for 20 min at 23° C., then add CH3 l (777 μL, 12.5 mmol, 2.0 eq). After 1 h, pour the mixture onto a pad of silica gel packed with hexane:EtOAc (1:1) (500 mL) and concentrate the filtrate to give 2.1 g (6.25 mmol, >99%) of N-[2-(3,4-dichlorophenyl)-3-butenyl]-N-methyl benzamide as a light yellow liquid.

Workup

  1. washWash
  2. waitAfter 1 h
  3. additionpour the mixture onto a pad of silica gel
  4. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-dbb1050feaa947a4a72e7fea9e3b1e1e
Source dataset
uspto-grants-1998_08
Patent number
US05789422

Reaction notes

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