Ethanol → HCID 12687119, compound

HRID 866938Notes

Reaction equation

HRID 866938 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:13]2[CH2:14][CH:15](Cl)[C:16]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:17]=3[S:18][C:12]=2[CH:11]=[CH:10][CH:9]=1.C(O)C.O>O1CCCC1>[F:23][C:21]1[CH:20]=[CH:19][C:17]2[S:18][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([Cl:7])[C:13]=3[CH2:14][CH2:15][C:16]=2[CH:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 12687117HCID 12687117, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 12687119HCID 12687119, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.7g of lithium aluminum hydride was suspended in 20ml of tetrahydrofuran, to the resulting suspension was added dropwise with stirring 2.1g of 9-chloro-11-chloro-2-fluoro-10,11-dihydrodibenzo[b,f]thiepin dissolved in 10ml of anhydrous tetrahydrofuran and the mixture was stirred at room temperature for 0.5hr., further under reflux condition for 3.5 hrs., while preventing the moisture. After completion of the reaction, an excess of lithium aluminum hydride was decomposed by adding ethanol and water, and filtered off using celite. The filtrate was evaporated to obtain the residue, which was chromatographed on silica gel, eluted with chloroform, and there was obtained 1.2g(67.0% of yield) of 2-fluoro-9-chloro-10,11-dihydrodibenzo[b,f]thiepin as pale green viscous oily substance.

Workup

  1. additionwas added dropwise
  2. temperature, further under reflux condition for 3.5 hrs
  3. customAfter completion of the reaction
  4. filtrationfiltered off
  5. customThe filtrate was evaporated
  6. customto obtain the residue, which
  7. customwas chromatographed on silica gel
  8. washeluted with chloroform

Sources & evidence

ORD record
ord-56bada16db454475998a69216b1259cd
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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