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

HRID 974460
Notes
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Reaction equation

HRID 974460 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:9]([C:15]2[N:16]=[N:17][N:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:19]=2)[C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[C:9]([C:15]2[N:16]=[N:17][N:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:19]=2)[CH2:10][OH:11])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14723818ethyl 3,3-bis(4-fluorophenyl)-2-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-2-propenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 147239063,3-Bis(4-fluorophenyl)-2-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-2-propenol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of ethyl 3,3-bis(4-fluorophenyl)-2-[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-2-propenoate (2.0 g, 4.8 mmoles) in dry methylene chloride (10 mL) under argon at -78° C. was added 10 mL of diisobutylaluminum hydride solution (1.0 Molar solution in methylene chloride) over a period of three minutes. The reduction was allowed to proceed at -78° C. under argon for two hours. Analytical TLC eluted twice with 20% (v/v) ethyl acetate in hexanes showed no starting material at Rf =0.42 and a major spot at Rf =0.14 for desired product. The crude reaction mixture (at -78° C.) was diluted with 10 mL of 2N HCl followed by extractions with ethyl acetate (40 mL×2). The organic layers were combined, dried over MgSO4, evaporated under reduced pressure and dried under high vacuum at room temperature overnight to give the title compound which was used without further purification in the next step.

Workup

  1. washAnalytical TLC eluted twice with 20% (v/v) ethyl acetate in hexanes
  2. customThe crude reaction mixture (at -78° C.)
  3. extractionfollowed by extractions with ethyl acetate (40 mL×2)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customdried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-1ff93225ec8a40f3b8d7a97da9942ed4
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05068346

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes