HCID 18940884, compound → HCID 18940916, compound

HRID 356013Notes

Reaction equation

HRID 356013 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13][CH2:14][CH:15](OCC)OCC)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N1C2C=C3C=CSC3=CC=2CC1)(=O)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13][CH2:14][CH3:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 18940884HCID 18940884, compoundHCID 18940934HCID 18940934, compound

Product 1

HCID 18940916HCID 18940916, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of acetal (D5, 2.14 g, 6.9 mmol) in dry dichloromethane (80 ml) at -78° C. was added titanium tetrachloride (1.48 ml, 13.85 mmol) dropwise by syringe. The mixture was stirred for 2 h at -78° C., 2 h at 0° C. and then overnight at room temperature. The mixture was then washed with water, saturated sodium bicarbonate solution, then water again, dried and evaporated. The residue was taken up in hot dichloromethane and petrol was added to precipitate polar material as a gum. The liquor was decanted off and addition of petrol/decantation was repeated twice. The final liquor was evaporated to give a mixture of the title compound and 5-acetyl-6,7-dihydro-5H-thieno[2,3-f]indole (0.31 g), which was hydrolysed without separation.

Workup

  1. customovernight
  2. customat room temperature
  3. washThe mixture was then washed with water, saturated sodium bicarbonate solution
  4. dry with materialwater again, dried
  5. customevaporated
  6. additionpetrol was added
  7. customto precipitate polar material as a gum
  8. customThe liquor was decanted off
  9. additionaddition of petrol/decantation
  10. customThe final liquor was evaporated
  11. customto give

Sources & evidence

ORD record
ord-f6f9cd39b899447fa93b90b983e1d940
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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