ethyl 3,3-bis(4-fluorophenyl)-2-[2-triphenylmethyl-2H-tetrazol-5-yl]-2-propenoate → HCID 14724008, compound

HRID 330686Notes

Reaction equation

HRID 330686 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)=[C:9]([C:15]2[N:16]=[N:17][N:18]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)=[C:9]([C:15]2[N:16]=[N:17][N:18]([C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:19]=2)[CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14723819ethyl 3,3-bis(4-fluorophenyl)-2-[2-triphenylmethyl-2H-tetrazol-5-yl]-2-propenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14724008HCID 14724008, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3 g (5 mmol) ethyl 3,3-bis(4-fluorophenyl)-2-[2-triphenylmethyl-2H-tetrazol-5-yl]-2-propenoate in 50 mL of methylene chloride at -70° C., 10 mL (15 mmol) diisobutylaluminium hydride solution (1.5M in methylene chloride) was added and the solution stirred for 3 hours. The reaction was quenched with water and the mixture extracted with methylene chloride. The combined organic fractions were dried with magnesium sulfate and concentrated in vacuo to give 2.1 g of the title compound; m.p.=176°-178° C.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture extracted with methylene chloride
  3. dry with materialThe combined organic fractions were dried with magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a626656d7d449f2b41ed3e5bdd7e42e
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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