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Iodoethane → Ethyl 3,3-bis(4-fluorophenyl)-2-(2-ethyl-2H-tetrazol-5-yl)-2-propenoate

HRID 1195345
Notes
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Reaction equation

HRID 1195345 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:9]([C:15]2[NH:19][N:18]=[N:17][N:16]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:30][CH3:31]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:9]([C:15]2[N:16]=[N:17][N:18]([CH2:30][CH3:31])[N:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydride2×HCID 178470939HCID 178470939, compound

Product 1

HCID 14723821Ethyl 3,3-bis(4-fluorophenyl)-2-(2-ethyl-2H-tetrazol-5-yl)-2-propenoateYield 45.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 10.0 g (0.028 mole) of ethyl 3,3-bis(4-fluorophenyl)-2-(1H-tetrazol-5-yl)-2-propenoate [prepared in Example 2] in 75 mL of N,N-dimethylformamide was added 1.2 g of 60% sodium hydride (0.03 mole) in mineral oil was added. After stirring for 0.5 hour, the sodium hydride had dissolved and 8.5 g (0.056 mole) of iodoethane was added. The solution was stirred at room temperature for 16 hours, diluted to 400 mL with water and extracted with CH2Cl2. The extracts were dried and concentrated in vacuo. The residue was triturated with hexane to remove mineral oil. The residue was absorbed onto silica gel by dissolving in CH2Cl2 and adding dry silica gel, then concentrating in vacuo to a dry powder. This material was transferred to the top of a silica gel column and eluted with 10% (v/v) ethyl acetate in hexane to give 4.9 g (45.5%) of the title compound; m.p.= 113°-114.5° C.

Workup

  1. additionwas added
  2. stirringThe solution was stirred at room temperature for 16 hours
  3. extractionextracted with CH2Cl2
  4. customThe extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with hexane
  7. customto remove mineral oil
  8. customThe residue was absorbed onto silica gel
  9. dissolutionby dissolving in CH2Cl2
  10. additionadding dry silica gel
  11. concentrationconcentrating in vacuo to a dry powder
  12. washeluted with 10% (v/v) ethyl acetate in hexane

Sources & evidence

ORD record
ord-9445bdfda3e041d2b9ebed59f8b7b944
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05110940

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes