2-Methyl-3-butyn-2-ol → HCID 54574602, compound

HRID 1080563Notes

Reaction equation

HRID 1080563 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7](I)=[C:6]([F:12])[CH:5]=1)[CH2:2][CH3:3].[CH3:13][C:14]([OH:18])([C:16]#[CH:17])[CH3:15].[I-]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu].C(N(CC)CC)C>[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([C:17]#[C:16][C:14]([CH3:15])([OH:18])[CH3:13])=[C:6]([F:12])[CH:5]=1)[CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 30165Iodide IonHCID 18979647HCID 18979647, compound

Product 1

HCID 54574602HCID 54574602, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 2 g of 1-propyl-3,5-difluoro-4-iodobenzene, 0.626 g of 2-methyl-3-butyn-2-ol, 0.164 g of tetrakis(triphenylphosphine)palladium(0), 10 ml of triethylamine and 0.054 g of copper(l) iodide was stirred at 90° for 2 hours. Then, the cooled reaction mixture was partitioned between water and ether, the ether phase was washed several times with water, dried over magnesium sulphate, filtered over Celite and evaporated on a rotary evaporator. The residue was then chromatographed on 75 g of silica gel (eluent: 10% ethyl acetate in hexane) and again evaporated. There were obtained 1.5 g of 4-(4-propyl-2,6-difluorophenyl)-2-methylbutyn-2-ol as a yellow liquid.

Workup

  1. customThen, the cooled reaction mixture
  2. customwas partitioned between water and ether
  3. washthe ether phase was washed several times with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered over Celite
  6. customevaporated on a rotary evaporator
  7. customThe residue was then chromatographed on 75 g of silica gel (eluent: 10% ethyl acetate in hexane)
  8. customagain evaporated

Sources & evidence

ORD record
ord-d532522f2c61438ca3d08df64a9b43ce
Source dataset
uspto-grants-1996_12
Patent number
US05582767

Reaction notes

Loading…