Trimethylsilylacetylene → HCID 59708590, compound

HRID 1809147Notes

Reaction equation

HRID 1809147 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9]([OH:11])=[O:10])=[N+:2]=[N-:3].[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>>[CH3:15][Si:16]([CH3:18])([CH3:17])[C:19]1[N:3]=[N:2][N:1]([C:4]2[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=2)[O:7][CH2:8][C:9]([OH:11])=[O:10])[CH:20]=1

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 59708701HCID 59708701, compound

Product 1

HCID 59708590HCID 59708590, compoundYield 61%

Procedure

To a 15 mL sealed tube was added (3-azidophenoxy)-acetic acid 5 (527 mg, 2.73 mmol, 1.0 eq.) and trimethylsilylacetylene (10 mL) and a stirbar. The tube was sealed and reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and solid was washed with ethyl ether to yield a dark gray solid (483 mg, 61%). 1H-NMR, Varian 400 MHz (DMSO-d6) δ 13.11 (bs, 1H), 8.86 (s, 1H), 7.52-7.46 (m, 3H), 7.03-7.00 (m, 1H), 4.80 (d, 2H), 0.31 (s, 9H) ppm.

Workup

  1. customTo a 15 mL sealed tube
  2. customThe tube was sealed
  3. customreaction mixture
  4. filtrationThe reaction mixture was filtered
  5. washsolid was washed with ethyl ether

Sources & evidence

ORD record
ord-12e6b537f48e4ae08f9d5d67988ba3a8
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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