Tetrahydrofuran → HCID 21543772, compound

HRID 1606578Notes

Reaction equation

HRID 1606578 reaction equation
[Br-:1].[NH:2]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][P+:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][N:4]=[N:3]1.O1CCC[CH2:31]1.[N+:35](=[CH2:37])=[N-:36]>CCOCC>[Br-:1].[CH3:31][N:5]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][P+:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:2][N:3]=[N:4]1.[Br-:1].[CH3:37][N:35]1[N:2]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][P+:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=[N:36]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 9550DiazomethaneHCID 178419402HCID 178419402, compound

Product 2

HCID 21543772HCID 21543772, compoundHCID 21543802HCID 21543802, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the 4-(tetrazol-5-yl)butyltriphenylphosphonium bromide prepared in Example I (4.65 g.; 10.0 m moles) in 50 ml. of dry tetrahydrofuran is added a solution of diazomethane in ether until the reaction solution remains yellow for 5 minutes. Concentration followed by chromatographic purification affords the desired 4-(1-N-methyltetrazol-5-yl)butyltriphenylphosphonium bromide and 4-(3-N-methyltetrazol-5-yl)butyltriphenylphosphonium bromide.

Workup

  1. concentrationConcentration
  2. customfollowed by chromatographic purification

Sources & evidence

ORD record
ord-6e516e4553704cf2889687f15b698bae
Source dataset
uspto-grants-1976_04
Patent number
US03953466

Reaction notes

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