Water → HCID 462653, compound

HRID 1080898Notes

Reaction equation

HRID 1080898 reaction equation
[N:1]([CH2:4][C:5]1[S:6][S:7][C:8]([CH2:11]O[Si](C(C)(C)C)(C)C)=[CH:9][CH:10]=1)=[N+:2]=[N-:3].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:40]C(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[N:1]([CH2:4][C:5]1[S:6][S:7][C:8]([CH2:11][Cl:40])=[CH:9][CH:10]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 94429TriphosgeneHCID 10448426HCID 10448426, compound

Product 1

HCID 462653HCID 462653, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the silyloxyazide 15 (100 mg; 0.31 mmol) in distilled THF (5 mL) was added at room temperature water (6.7 μL), followed by the sequential addition, in one portion, of triphenylphosphine (97 mg; 0.37 mmol) and triphosgene (460 mg; 1.55 mmol). The reaction mixture was shielded from light and stirred at room temperature overnight. The reaction mixture was chromatographed on silica gel, eluting with 10% ethyl acetate in hexane, to afford 27.4 mg (40.4%) of the title chloride 28. 1H NMR (CDCl3) δ6.425 (dd, J=6.4, 6.0 Hz, 2H, C=CH), 4.267 (s, 2H, CH2), 4.004 (s, 2H, CH2); 13C NMR (CDCl3) δ128.538, 28.417, 127.719, 127.582, 54.864, 46.634.

Workup

  1. customThe reaction mixture was chromatographed on silica gel
  2. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-860fd82ab3864f9b94b6e070250f3876
Source dataset
uspto-grants-1996_12
Patent number
US05583235

Reaction notes

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