Ethyl bromoacetate → HCID 20037807, compound

HRID 1904675Notes

Reaction equation

HRID 1904675 reaction equation
[Na].[OH:2][CH:3]([C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[O:12][CH2:13][C:14]1[CH:15]=[C:16]([C:20]2[N:21]=[N:22][NH:23][N:24]=2)[CH:17]=[CH:18][CH:19]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(O)C>[OH:2][CH:3]([C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[O:12][CH2:13][C:14]1[CH:15]=[C:16]([C:20]2[N:21]=[N:22][N:23]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:24]=2)[CH:17]=[CH:18][CH:19]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545SodiumHCID 14501723HCID 14501723, compound

Product 1

HCID 20037807HCID 20037807, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.3 g of sodium in 60 ml of ethanol was added 4.3 g of 5[3-[3-(1-hydroxyhexyl)phenoxymethyl]phenyl]-2H-tetrazole and 2.0 g of ethyl bromoacetate. The mixture was refluxed for 18 hours. The solvent was evaporated and the residue was partitioned between ether and water. The ether layer was dried and evaporated to give 4.5 g of a viscous oil. This was passed through a short silica gel column and eluted with chloroform:methanol (4:1). The product (2.3 g) was obtained as a light amber oil.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between ether and water
  4. dry with materialThe ether layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-a23c98b6446d4459b0a9637fc624e1b4
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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