tert-Butanol → (4-Phenyl-but-3-ynyl)-carbamic acid tert-butyl ester

HRID 6723

Reaction equation

HRID 6723 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][CH2:10]C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:21])C=CC=CC=1.C([N:33]([CH2:36]C)CC)C.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1>[C:38]([O:42][C:36](=[O:21])[NH:33][CH2:10][CH2:9][C:8]#[C:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 109759835-phenylpent-4-ynoic Acid

Product 1

HCID 23544319(4-Phenyl-but-3-ynyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-phenylpent-4-ynoic acid (0.49 g), diphenylphosphoryl azide (0.66 mL) and triethylamine (0.43 mL) was refluxed in 15 mL toluene for 3 h. The reaction was cooled to rt and t-butyl alcohol was added. The reaction was refluxed for 16 h, then the volatile materials were removed via a rotary evaporator. The residue was purified by column chromatography on silica (2–6% ethyl acetate in hexanes) to give (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester (0.3 g).

Workup

  1. temperatureThe reaction was refluxed for 16 h
  2. customthe volatile materials were removed via a rotary evaporator
  3. customThe residue was purified by column chromatography on silica (2–6% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5939bb060647439fbc9218ef92c27765
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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