Toluene → HCID 86714680, compound

HRID 1409474Notes

Reaction equation

HRID 1409474 reaction equation
[N+:1](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-:2].[CH3:9][CH:10]([OH:13])[C:11]#[CH:12].[C:14]1(C)C=CC=CC=1>>[OH:13][CH:10]([CH3:9])[CH2:11][C:12]1[NH:2][N:1]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:14]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 12192Ethyl diazoacetateHCID 162393-Butyn-2-ol

Product 1

HCID 86714680HCID 86714680, compound

Conditions

Temperature
100 °C

Procedure

Into a flask containing ethyl diazoacetate (52.63 mmol, 6 g) in toluene (100 ml), 3-butyn-2-ol (78.94 mmol, 6.6 g) was added at RT and stirred at 100° C. for 5 h. The solvent was evaporated and the crude was purified by flash-chromatography. Yield 697 mg. 1H-NMR (400 MHz; CDCl3): δ 1.22-1.28 (m, 3H), 1.39 (t, 3H), 2.72-2.78 (m, 1H), 2.82-2.91 (m, 1H), 4.10-4.17 (m, 1H), 4.38 (q, 2H), 6.64 (s, 1H).

Workup

  1. additionwas added at RT
  2. customThe solvent was evaporated
  3. customthe crude was purified by flash-chromatography

Sources & evidence

ORD record
ord-83e1ef2bb8e94a988be9d6b996af0ed7
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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