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 330642Notes

Reaction equation

HRID 330642 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

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 6344DichloromethaneSolvent

Procedure

To a stired 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 minues. The reduction was llowed 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 misture (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 misture (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-a8f6a0bdbff84be99907042146d071ba
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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