Chloroform → (8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl)methyl 4-methylbenzene-1-sulfonate

HRID 2116759Notes

Reaction equation

HRID 2116759 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14][CH:13]([CH2:16][OH:17])[O:12][C:8]3=2)[N:3]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].C(N(CC)CC)C.C(Cl)(Cl)Cl>C(Cl)Cl.O>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:17][CH2:16][CH:13]2[O:12][C:8]3=[C:9]4[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14]2)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]4)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21892068[8-Methyl-2,3-Dihydro[1,4]Dioxino[2,3-f]Quinolin-2-yl]Methanol

Product 1

HCID 21892063(8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl)methyl 4-methylbenzene-1-sulfonateYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol (0.13 g, 0.57 mmol), tosyl chloride (0.16 g, 0.82 mmol) and triethylamine (0.65 mL, 4.7 mmol) in CH2Cl2 (8 mL) was stirred at room temperature for 18 h. CHCl3 (30 mL) and H2O (30 mL) were added. The two layers were separated. The aqueous layer was extracted with CHCl3 (20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification on SiO2, eluting with (1:1) hexane:EtOAc gave 0.19 g (88%) of the title compound as a brown syrup.

Workup

  1. customThe two layers were separated
  2. extractionThe aqueous layer was extracted with CHCl3 (20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification on SiO2
  7. washeluting with (1:1) hexane

Sources & evidence

ORD record
ord-498b4e0c32534fa0b7a68a9181de046c
Source dataset
uspto-grants-2008_10
Patent number
US07439364B2

Reaction notes

Loading…