1-Acetoxy-2-bromoethane → Ethyl 4'-(2-acetoxyethoxy)-3''-tert-butyl-4''-diethylamino[1,1';3',1'']terphenyl-4-carboxylate

HRID 1261521Notes

Reaction equation

HRID 1261521 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][CH:24]=3)[CH:19]=[CH:20][C:21]=2[OH:22])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:36]([O:39][CH2:40][CH2:41]Br)(=[O:38])[CH3:37].[Cl-].[NH4+]>CN(C)C=O>[C:36]([O:39][CH2:40][CH2:41][O:22][C:21]1[CH:20]=[CH:19][C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][CH:24]=2)=[CH:17][C:16]=1[C:7]1[CH:8]=[CH:9][C:10]([N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:6]=1)(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11676663Ethyl 3''-tert-butyl-4''-diethylamino-4'-hydroxy[1,1';3',1'']terphenyl-4-carboxylate

Product 1

HCID 66672106Ethyl 4'-(2-acetoxyethoxy)-3''-tert-butyl-4''-diethylamino[1,1';3',1'']terphenyl-4-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

850 mg (1.9 mmol) of ethyl 3″-tert-butyl-4″-diethylamino-4′-hydroxy[1,1′;3′,1″]terphenyl-4-carboxylate (obtained in Example 1d) are dissolved in dimethylformamide under nitrogen. 92 mg (2.3 mmol) of 60% sodium hydride are added. After 20 minutes at room temperature, 0.25 mL (2.3 mmol) of 2-bromoethan-1-ol acetate are added and the mixture is stirred for 24 hours at room temperature and then poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and then dried and evaporated. The residue obtained is purified by chromatography on silica gel (eluent: 70/30 heptane/ethyl acetate). 1 g of ethyl 4′-(2-acetoxyethoxy)-3″-tert-butyl-4″-diethylamino[1,1′;3′,1″]terphenyl-4-carboxylate is obtained (yield=99%) in the form of a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. customdried
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on silica gel (eluent: 70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-7f4b93efc60e4150983c6117ee5f3bb8
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

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