2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 58635311, compound

HRID 1012866Notes

Reaction equation

HRID 1012866 reaction equation
[N:1]([C@H:4]([CH2:14][CH2:15][O:16]C1C=CC(OC)=CC=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+:2]=[N-:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl.O>[NH2:1][C@@H:4]([CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH2:14][CH2:15][OH:16].[N:1]([C@@H:4]([CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH2:14][CH2:15][OH:16])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86594471HCID 86594471, compound

Product 2

HCID 58635311HCID 58635311, compoundHCID 86594470HCID 86594470, compound

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of {[(2R)-2-azido-4-(4-methoxyphenoxy)butyl]oxy}(tert-butyl)dimethylsilane (4.7 g, 12.86 mmol) in 19:1 DCM/water at 0° C. was added DDQ (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone) (3.5 g, 15.43 mmol, 1.2 eq) and the mixture was stirred (from 0° C. to rt) until all starting material disappeared as indicated by TLC (thin layer chromatography) analysis. Most DCM was then removed in vacuo and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and saturated NaHCO3 repeatedly until a pale yellow organic solution was obtained. The organic solution was dried and the crude was purified by silica gel chromatography (5% acetone/toluene) to give the desired product (3R)-3-azido-4-{[tert-butyl(dimethyl)silyl]oxy}butan-1-ol. 1H NMR (400 MHz, Acetone-d6): δ3.89 (1 H, dd), 3.73-3.65 (5 H, m), 1.76-1.68 (1 H, m), 1.62-1.54 (1 H, m), 0.94 (9 H, s), 0.13 (6 H, s).

Workup

  1. customMost DCM was then removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe ethyl acetate solution was washed with water and saturated NaHCO3 repeatedly until a pale yellow organic solution
  4. customwas obtained
  5. customThe organic solution was dried
  6. customthe crude was purified by silica gel chromatography (5% acetone/toluene)

Sources & evidence

ORD record
ord-0f8d87b4d288453486ec299485e49f7c
Source dataset
uspto-grants-2011_07
Patent number
USRE042562E1

Reaction notes

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