Dichloromethane → HCID 20079678, compound

HRID 1654123Notes

Reaction equation

HRID 1654123 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1.C(Cl)Cl.[C:15]([Mg]Br)#[CH:16].P([O-])(O)(O)=O.[Na+]>O1CCCC1>[F:11][C:2]([F:10])([F:1])[C:3]1[O:7][C:6]([CH:8]([OH:9])[C:15]#[CH:16])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 75376655-(trifluoromethyl)furan-2-carbaldehydeHCID 23672064Monosodium phosphateHCID 178418486HCID 178418486, compound

Product 1

HCID 20079678HCID 20079678, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of approximately 1.78 g of the product of Stage D and approximately 20 ml of methylene chloride was cooled to +5° C. and 27 ml of ethynylmagnesium bromide as a 0.5M solution in tetrahydrofuran were added over 15 minutes. The mixture was stirred for 15 minutes at +5° C., poured into an aqueous sodium dihydrogenphosphate solution and extracted with methylene chloride. The extract was dried, the solvent was evaporated at 30° C. and the residue was chromatographed on silica (eluent: methylene chloride) to obtain 0.87 g of the expected product.

Workup

  1. temperaturewas cooled to +5° C.
  2. extractionextracted with methylene chloride
  3. customThe extract was dried
  4. customthe solvent was evaporated at 30° C.
  5. customthe residue was chromatographed on silica (eluent: methylene chloride)

Sources & evidence

ORD record
ord-b5760096002e4bcfa039e10cedec5f92
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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