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

HRID 974498Notes

Reaction equation

HRID 974498 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) diisobutylaluminum hydride solution (1.5M in methylene chloride) was added and the solution stirred for 3 hours. The reaction is 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 is 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-654e21af0c264ca8a6770a1d2aed2b44
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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