3-Methylbut-1-yne → HCID 67036292, compound

HRID 1623481Notes

Reaction equation

HRID 1623481 reaction equation
[CH3:1][CH:2]([CH3:5])[C:3]#[CH:4].[Li]CCCC.[I:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]=[O:20]>C1COCC1.[Cl-].[Na+].O>[I:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:20])[C:4]#[C:3][CH:2]([CH3:5])[CH3:1]

Participants

6

Reactant 3

HCID 690193-Methylbut-1-yneHCID 27333851-Iodo-2-isocyanatobenzeneHCID 178418339Butyllithium

Product 1

HCID 67036292HCID 67036292, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

3-Methyl-but-1-yne (11 g, 0.16 mol) in THF (100 ml) was added n-BuLi (2.5M in hexane) (59 ml, 0.15 mol) at 0° C. The resulting mixture was stirred for 30 minutes. Then a solution of 1-iodo-2-isocyanato-benzene (33 g, 0.14 mol) in THF (100 ml) was dropped into the mixture. After stirring for 2 hours at 0° C., the mixture was treated with brine (100 ml) and extracted with ether (200 ml). The organic layer was dried over sodium sulfate and concentrated to give the crude product 4-methyl-pent-2-ynoic acid (2-iodo-phenyl)-amide (38 g, 90%) as a yellow oil which was used in next step without purification. MS calcd. for C12H12INO 313.1, obsd. (ESI+) [(M+H)+] 314.0.

Workup

  1. stirringAfter stirring for 2 hours at 0° C.
  2. extractionextracted with ether (200 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1da5cdecd80a447d804535499e05d547
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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