Tributyltin azide → HCID 178420216, compound

HRID 1535051Notes

Reaction equation

HRID 1535051 reaction equation
[C:1]([C:3]1[CH:37]=[CH:36][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]2[C:27]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][C:14]3[CH2:15][CH:16]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:17][C:13]=3[CH:12]=2)=[CH:5][CH:4]=1)#[N:2].C([Sn]([N:51]=[N+:52]=[N-:53])(CCCC)CCCC)CCC>>[NH:51]1[C:1]([C:3]2[CH:37]=[CH:36][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]3[C:27]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][C:14]4[CH2:15][CH:16]([CH2:18][CH2:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[O:17][C:13]=4[CH:12]=3)=[CH:5][CH:4]=2)=[N:2][N:53]=[N:52]1

Participants

3

Reactant 2

HCID 4984872Tributyltin azideHCID 15161043HCID 15161043, compound

Product 1

HCID 178420216HCID 178420216, compound

Procedure

A mixture of 6-[3-(4-cyanophenoxy)propyl]-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran E22 (1 gm, 2.0 mmoles) and tri-n-butyl tin azide (2.2 gm; 6.6 mmoles) was heated in an oil bath at 125° C. for 90 minutes. The total mixture was chromatographed on silica gel using 1:1 ethyl acetate in hexane and containing 10% acetic acid to yield 1.2 gm of 6-{3-[4-(1H-tetrazol-5-yl)phenoxy]propyl}-5-benzyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E23.

Workup

  1. customThe total mixture was chromatographed on silica gel using 1:1 ethyl acetate in hexane
  2. additioncontaining 10% acetic acid

Sources & evidence

ORD record
ord-158b25549904461db0b4fc66ecb5b5c3
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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