HCID 15661031, compound → HCID 15661032, compound

HRID 1087390Notes

Reaction equation

HRID 1087390 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]2[S:8](=[O:22])(=[O:21])[C:9]3[CH:16]=[C:15]([C:17](OC)=[O:18])[CH:14]=[CH:13][C:10]=3[CH2:11][CH2:12][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[CH3:25][N:26]([Al](C)C)[CH3:27]>C1(C)C=CC=CC=1>[CH3:25][N:26]([CH3:27])[C:17]([C:15]1[CH:14]=[CH:13][C:10]2[CH2:11][CH2:12][C:6]3[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:24]=[CH:23][C:7]=3[S:8](=[O:22])(=[O:21])[C:9]=2[CH:16]=1)=[O:18]

Participants

4

Reactant 2

HCID 15661031HCID 15661031, compoundHCID 16686364HCID 16686364, compound

Product 1

HCID 15661032HCID 15661032, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of the ester from Step 1 (440 mg, 1.28 mmol) in dry toluene (5 mL) was added dropwise at room temperature a solution of N,N-dimethylamino dimethyl aluminum 0.8M in toluene (16 mL, 12.8 mmol). The resulting solution was heated to 70° C. for 2 hours. The reaction mixture was then cooled to 0° C. and quenched with excess ethyl acetate followed by addition of lN aqueous HCl. The solvents were removed under reduced pressure and the resulting solid was filtered, washed with ethyl acetate to afford the title product which was used as such for the next step.

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customquenched with excess ethyl acetate
  3. additionfollowed by addition of lN aqueous HCl
  4. customThe solvents were removed under reduced pressure
  5. filtrationthe resulting solid was filtered
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ec89e1f57f194a889f04874b03a40813
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Reaction notes

Loading…