4-Methylmorpholine → HCID 20096939, compound

HRID 1769678Notes

Reaction equation

HRID 1769678 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[OH:6][CH:7]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=1)=[O:9].CN1CCOCC1>ClCCl>[Br:1][CH2:2][C:3]([O:9][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=1)[C:7]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=1)=[O:6])=[O:4]

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 89602Bromoacetyl chlorideHCID 150442041,2-Bis(4-ethylphenyl)-2-hydroxyethanone2×

Product 1

HCID 20096939HCID 20096939, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromoacetyl chloride (2.00 mL, 24.2 mmol) in anhydrous dichloromethane (20 mL) was added dropwise to a cold (0° C.) mixture of 2-hydroxy-1,2-di-(4-ethylphenyl)ethanone (IX; 6.5 g, 24.2 mmol) and N-methylmorpholine (NMM; 2.7 mL, 24.2 mmol) in anhydrous dichloromethane (180 mL). The mixture was stirred at 0° C. for 1 hour and at ambient temperature for 2 hours before additional 2-hydroxy-1,2-di-(4-ethylphenyl)ethanone (0.5 mL) and NMM (0.6 mL) were added to aid in completeion. After 1 hour, the mixture was washed with saturated sodium bicarbonate solution, 1N HCl and brine. Following drying and solvent evaporation, the residue was purified by flash chromatography on silica gel (gradient elution with 10% ethyl acetate in hexanes followed by 25% ethyl acetate in hexanes) and furnished 6.10 g (65%) of bromoacetoxy-1,2-di(4-ethylphenyl)ethanone as a pal-yellow oil which was used in subsequent reactions without further purification.

Workup

  1. additionwere added to aid in completeion
  2. washthe mixture was washed with saturated sodium bicarbonate solution, 1N HCl and brine
  3. customFollowing drying
  4. customsolvent evaporation
  5. customthe residue was purified by flash chromatography on silica gel (gradient elution with 10% ethyl acetate in hexanes followed by 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-06cd49ed56b44e89824d1b669bb91cbd
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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