HCID 20079667, compound → HCID 20079651, compound

HRID 1654121Notes

Reaction equation

HRID 1654121 reaction equation
[C:1]([Mg]Br)#[CH:2].[F:5][C:6]([F:23])([F:22])[C:7]1[O:8][C:9]([CH2:20]Br)=[CH:10][C:11]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.P([O-])(O)(O)=O.[Na+]>O1CCCC1.[Cu](Cl)Cl>[F:23][C:6]([F:5])([F:22])[C:7]1[O:8][C:9]([CH2:20][C:1]#[CH:2])=[CH:10][C:11]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1

Participants

6

Reactant 3

HCID 20079667HCID 20079667, compoundHCID 23672064Monosodium phosphateHCID 178418486HCID 178418486, compound

Product 1

HCID 20079651HCID 20079651, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

90 ml of ethynyl magnesium bromide as a 1M solution in tetrahydrofuran and 1.8 g of copper chloride were added to 6.18 g of the product of Stage E in 15 ml of tetrahydrofuran and the mixture was refluxed for 18 hours, cooled to 20° C., poured into a saturated aqueous sodium dihydrogenphosphate solution, and extracted with isopropyl ether. The extract was dried and the solvent evaporated. The residue was chromatographed on silica (eluent: 9/1 hexane/isopropyl ether) to obtain 1.5 g of the expected product.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. extractionextracted with isopropyl ether
  3. customThe extract was dried
  4. customthe solvent evaporated
  5. customThe residue was chromatographed on silica (eluent: 9/1 hexane/isopropyl ether)

Sources & evidence

ORD record
ord-86f7510c70c84a268504b093210ea9f4
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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