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 1195346Notes

Reaction equation

HRID 1195346 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-f3f913a4e17d48608e43b4b944c668a3
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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