tert-Butanol → tert-Butyl 3-butyn-1-ylcarbamate

HRID 1965963Notes

Reaction equation

HRID 1965963 reaction equation
C([N:3]([CH2:6]C)[CH2:4][CH3:5])C.[C:8](O)(=O)[CH2:9]CC#C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.[C:32]([OH:36])([CH3:35])([CH3:34])[CH3:33]>>[C:32]([O:36][C:6](=[O:22])[NH:3][CH2:4][CH2:5][C:8]#[CH:9])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 224644-Pentynoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 10725815tert-Butyl 3-butyn-1-ylcarbamateYield 53%

Conditions

Temperature
85 °C

Procedure

Add triethylamine (3 mL) to a solution of 4-pentynoic acid (1.96 g, 20 mmol) in tert-butanol (6 mL) at 0° C. and then add diphenyl phosphoryl azide (CAUTION: reaction starts violently a short period after the addition). Heat the reaction mixture at 85° C. overnight under nitrogen. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with dichloromethane to obtain the title compound as a white solid (1.81 g, 53%).

Workup

  1. waitstarts violently a short period
  2. additionafter the addition)
  3. concentrationConcentrate in vacuo
  4. custompurify the crude mixture by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-246c734524484f258c205dc0f904f54d
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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