Ethyl Acetate → HCID 69517064, compound

HRID 1297209Notes

Reaction equation

HRID 1297209 reaction equation
[C:1]([N:20]1[N:24]=[N:23][C:22]([CH2:25][C:26]#[N:27])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([CH:31]([CH2:34][CH2:35][CH3:36])[CH:32]=O)[CH2:29][CH3:30].[OH-].[Na+].CCOC(C)=O>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:28]([CH:31]([CH2:34][CH2:35][CH3:36])[CH:32]=[C:25]([C:22]1[N:23]=[N:24][N:20]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:21]=1)[C:26]#[N:27])[CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 875602-PropylvaleraldehydeHCID 58914637HCID 58914637, compound

Product 1

HCID 69517064HCID 69517064, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of (2-trityl-2H-tetrazol-5-yl)-acetonitrile (2.0 g, 5.69 mmol) in 25 mL benzene was added 2-n-propylvaleraldehyde (0.87 g, 6.79 mmol), 25 mL 10% NaOH (aq), and tetrabutylammonium bromide (50 mg). The mixture was stirred for 1 h, then poured into EtOAc. The phases were separated, and the organic phase dried (MgSO4) and concentrated. Flash chromatography of the residue (10→15% EtOAc/hexanes) provided 1.66 g (64%) of 4-propyl-2-(2-trityl-2H-tetrazol-5-yl)-hept-2-enenitrile as a colorless solid. 1H NMR (CDCl3) δ 7.34 (m, 10H, —CHCH═C—), 7.09 (m, 6H), 2.86 (m, 1H, —CH2CH—), 1.30-1.59 (m, 8H, —CH2CH2—), 0.90 (t, J=7.1 Hz, 6H, CH3—).

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-76b1eda13cdc4c08a6a1ab7d67fe72ec
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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