Sodium Chloride → HCID 15679123, compound

HRID 2165219Notes

Reaction equation

HRID 2165219 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1.C([Li])CCC.CN(C)[CH:26]=[O:27].[Cl-].[Na+]>O1CCCC1.CCCCCC>[F:9][C:5]1[C:4]([F:10])=[C:3]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[C:2]([F:1])=[C:7]([F:8])[C:6]=1[CH:26]=[O:27]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 15679122HCID 15679122, compoundHCID 178418339Butyllithium

Product 1

HCID 15679123HCID 15679123, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-55 °C

Procedure

13 g of 2-[(2,3,5,6-tetrafluorophenyl)-methoxy]-tetra hydropyran in 200 ml of tetrahydrofuran were cooled to -60 C. and 35.1 ml of butyllithium (1,6M) in hexane were added dropwise over the course of 30 minutes. The mixture was stirred for 1 hour at -55° C. and 5 ml of dimethylformamide dissolved in 10 ml of tetrahydrofuran were added over the course of 5 minutes. The mixture was stirred for 1/2hours at this temperature and 50 ml of a saturated aqueous sodium chloride solution were added. Extraction was carried out with isopropyl ether and the extract was dried and the solvents removed under reduced pressure to obtain 14.4 g of the expected product which was used as is in the following step.

Workup

  1. additionwere added over the course of 5 minutes
  2. additionwere added
  3. extractionExtraction
  4. customthe extract was dried
  5. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-37e41c98c81d4329b13dbbb6fb7a0879
Source dataset
uspto-grants-1990_07
Patent number
US04939172

Reaction notes

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