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Triethylamine → 5-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 909309
Notes
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Reaction equation

HRID 909309 reaction equation
[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:22])=[CH:6][C:7]([CH3:21])([CH3:20])[NH:8]2.C(N(CC)CC)C.[F:30][C:31]([F:37])([F:36])[S:32](Cl)(=[O:34])=[O:33]>ClCCl.C(Cl)(Cl)Cl>[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][S:32]([C:31]([F:37])([F:36])[F:30])(=[O:34])=[O:33])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:22])=[CH:6][C:7]([CH3:21])([CH3:20])[NH:8]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 579906105-Hydroxymethyl-6-(2-hydroxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 584854825-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 42%

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-Hydroxymethyl-6-(2-hydroxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-1,293 mg, 0.992 mmol) was dissolved in anhydrous dichloromethane (5 mL) and then triethylamine (167 μL, 1.20 mmol) and trifluoromethanesulfonyl chloride (106 μL, 0.996 mmol) were added thereto at 0° C. After the reaction mixture was stirred at 0° C. for 1 hour, it was diluted with chloroform (20 mL). The whole was washed with saturated aqueous NaHCO3 solution (20 mL) and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (177 mg) as an orange solid. (Yield 42%)

Workup

  1. customat 0° C
  2. washThe whole was washed with saturated aqueous NaHCO3 solution (20 mL)
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-363e7c4ce3414164848876eec1a24e02
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08017775B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes