Diethyl Ether → HCID 14987370, compound

HRID 2082371Notes

Reaction equation

HRID 2082371 reaction equation
[CH:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([C:45]([O-:47])=[O:46])=[CH:5][CH:4]=1)=[O:2].[CH2:48]([Mg]Br)[CH3:49].[CH3:52][CH2:53]OCC>>[OH:2][CH:1]([C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:5][CH:4]=1)[CH2:52][CH3:53]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 19023931HCID 19023931, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 14987370HCID 14987370, compoundYield 95%

Procedure

Into a solution of 5-formyl-1-[2'-(1-triphenylmethyltetrazol-5-yl)biphenyl-4-yl-methyl]pyrrole-2-carboxylate (2.0 g, 3.1 mmol) in dry ether (100 ml) cooled to -78° C. was syringed a solution of ethyl magnesium bromide (1.3 ml of a 3.0M solution in ether; 4.0 mmol) dropwise over 10 minutes. The mixture was allowed to stir for 2 hours while being allowed to warm to room temperature. The mixture was quenched with 10% aqueous ammonium chloride (20 ml) and the organic phase was washed with saturated aqueous sodium bicarbonate (50 ml), saturated aqueous sodium chloride (50 ml) and dried (MgSO4) before being filtered and concentrated to leave 2.0 g (95%) of a white solid which could be chromatographed on silica gel but was generally used without further purification, being one spot by tlc.

Workup

  1. customThe mixture was quenched with 10% aqueous ammonium chloride (20 ml)
  2. washthe organic phase was washed with saturated aqueous sodium bicarbonate (50 ml), saturated aqueous sodium chloride (50 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationbefore being filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d4e758d34ce84d7aa0d40c07bfe87e26
Source dataset
uspto-grants-1993_02
Patent number
US05189048

Reaction notes

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