Benzyl Alcohol → Benzyl [1-(4-nitrobenzyl)but-3-enyl]carbamate

HRID 1584756Notes

Reaction equation

HRID 1584756 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]([CH2:13][CH:14]=[CH2:15])C(O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.C([N:37]([CH2:40]C)CC)C.[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([NH:37][C:40](=[O:25])[O:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:13][CH:14]=[CH2:15])=[CH:16][CH:17]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 224570092-(4-Nitrobenzyl)pent-4-enoic acid

Product 1

HCID 53992691Benzyl [1-(4-nitrobenzyl)but-3-enyl]carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(4-Nitrobenzyl)pent-4-enoic acid (9.3 g, 40.0 mmol) is treated in toluene with 11.55 g (42.0 mmol) of diphenylphosphoryl azide at 50° C. in the presence of triethylamine (5.6 ml, 40.0 mmol) and benzyl alcohol (5.18 g, 48.0 mmol). After 20 minutes, the temperature is slowly increased and the mixture is then boiled under reflux for a further 3 hours. After cooling, the reaction mixture is washed twice with 1N sodium hydroxide solution, twice with 1N hydrochloric acid and twice with brine, dried over sodium sulfate and evaporated on a rotary evaporator. The title compound is obtained as white crystals after crystallization of the crude product from toluene/hexane. M.p.: 94-95° C. TLC: ethyl acetate/hexane (1:3) Rf =0.22.

Workup

  1. temperaturethe temperature is slowly increased
  2. temperatureunder reflux for a further 3 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed twice with 1N sodium hydroxide solution, twice with 1N hydrochloric acid and twice with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-e246c553bc4848909cce11fb2dac40dd
Source dataset
uspto-grants-1999_08
Patent number
US05935951

Reaction notes

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