ethyl 3,3-bis(4-fluorophenyl)-2-(1-ethyl-1H-tetrazol-5-yl)-2-propenoate → 3,3-Bis(4-fluorophenyl)-2-(1-ethyl-1H-tetrazol-5-yl)-2-propenol

HRID 330648Notes

Reaction equation

HRID 330648 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[C:9]([C:15]2[N:19]([CH2:20][CH3:21])[N:18]=[N:17][N:16]=2)[C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)=[C:9]([C:15]2[N:19]([CH2:20][CH3:21])[N:18]=[N:17][N:16]=2)[CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14723820ethyl 3,3-bis(4-fluorophenyl)-2-(1-ethyl-1H-tetrazol-5-yl)-2-propenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 147238233,3-Bis(4-fluorophenyl)-2-(1-ethyl-1H-tetrazol-5-yl)-2-propenolYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3,3-bis(4-fluorophenyl)-2-(1-ethyl-1H-tetrazol-5-yl)-2-propenoate (1.0 g, 2.6 mmoles) at -78° in CH2Cl2 was rapidly added 7.8 mL (7.8 mmoles) of diisobutylaluminum hydride solution (1.0 Molar in methylene chloride). After stirring for 45 minutes, the mixture was quenched with 1N HCl solution. The organic layer was separated, dried (MgSO4) and concentrated in vacuo. The residual oil was triturated with hexane to give 0.9 g (100%) of the title compound; m.p.=103°-111° C.

Workup

  1. customat -78°
  2. customthe mixture was quenched with 1N HCl solution
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residual oil was triturated with hexane

Sources & evidence

ORD record
ord-35269d8d53d242f9b8ddee6dcbe437e2
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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