Acetate → HCID 118324348, compound

HRID 2206969Notes

Reaction equation

HRID 2206969 reaction equation
C(OCC[CH2:7][CH2:8][CH2:9][N:10]=[N+:11]=[N-:12])(=O)C.[C:13]([O-:16])([O-])=O.[K+].[K+].[C:19]([O-])(=O)C.[K]>CO.O>[N:10]([CH:9]([CH3:19])[CH2:8][CH2:7][CH2:13][OH:16])=[N+:11]=[N-:12]

Participants

7

Reactant 4

HCID 175AcetateHCID 11430Potassium CarbonateHCID 5462222PotassiumHCID 11159583HCID 11159583, compound

Product 1

HCID 118324348HCID 118324348, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

5.1 g of 4-azido-1-pentylacetate (4.46) (33 mmol, 1.0 eq) from Example 19 was dissolved in 30 mL of MeOH and 2 mL of water. This solution was then saturated with K2CO3 and stirred overnight at room temperature. The reaction was then checked by TLC to confirm conversion of the acetate to the primary hydroxyl. Water (300 mL) was added to dissolve the potassium salt and extracted with diethyl ether 3×100 mL. The organic extracts were combined and dried with MgSO4. The solution was filtered and concentrated under vacuum with no external heat resulting in 4-azido-1-pentanol 4.47: 65% Yield; 1H NMR (500 MHz, Acetone-d6): δ: d 3.56 (t, J=4.2 Hz, 2H), 3.45 (t, J=7 Hz, 2H), 1.69-1.37 (m, 6H)13C NMR (100 MHz, Acetone): δ: 62.19, 52.01, 33.17, 29.42, 23.90

Workup

  1. extractionextracted with diethyl ether 3×100 mL
  2. dry with materialdried with MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated under vacuum with
  5. temperatureno external heat
  6. customresulting in 4-azido-1-pentanol 4.47

Sources & evidence

ORD record
ord-0982509f0ff74451820a15b9fe2ede86
Source dataset
uspto-grants-2016_06
Patent number
US09376385B2

Reaction notes

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