2-Methyl-3-butyn-2-ol → HCID 86714628, compound

HRID 1409336Notes

Reaction equation

HRID 1409336 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].C(N(CC)CC)C.[N+:14](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N-:15]>FC(F)(F)S([O-])(=O)=O.[Zn+2].FC(F)(F)S([O-])(=O)=O.O>[OH:6][C:2]([C:4]1[NH:15][N:14]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=1)([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 12192Ethyl diazoacetate

Product 1

HCID 86714628HCID 86714628, compoundYield 27.9%

Reagents, catalysts & solvents 2

HCID 104671Zinc trifluoromethanesulfonateCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Zinc trifluoromethanesulfonate (2.378 mmol, 0.864 g), 2-methyl-3-butyn-2-ol (11.89 mmol, 1 g) and triethylamine (17.83 mmol, 1.804 g) were added into a flask under nitrogen atmosphere. Ethyl diazoacetate (14.27 mmol, 1.628 g) was added slowly and the temperature was carefully raised to 100° C. and stirred for 8 h. Water was added and the mixture was extracted twice with DCM. The combined DCM phases were dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.658 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.28 (t, 3H), 1.45 (s, 6H), 4.24 (q, 2H), 5.34 (s, 1H), 6.52 (s, 1H), 13.22 (bs, 1H).

Workup

  1. extractionthe mixture was extracted twice with DCM
  2. dry with materialThe combined DCM phases were dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-8d40ec6c48d44f1c8db99e8e4fe9a745
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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