Water → HCID 22161779, compound

HRID 1088806Notes

Reaction equation

HRID 1088806 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]([CH2:20][CH3:21])[CH2:17][CH2:16][C:15]2=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.O1CCC[CH2:25]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]([CH2:20][CH3:21])[CH2:17][CH2:16][C:15]2=[CH2:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 22161781HCID 22161781, compound

Product 1

HCID 22161779HCID 22161779, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 178418339ButyllithiumSolvent

Conditions

Temperature
-40 °C

Procedure

To a suspension of methyltriphenyl phosphonium bromide (11.85 g) in tetrahydrofuran (100 ml), n-butyl lithium (10.2 ml) was added dropwise with stirring in nitrogen flow at -40° C. The temperature was raised to -20° C. over 30 minutes, a solution of 8-(t-butyldimethylsilyloxymethyl)-4-oxo-1-ethyl-1,2,3,4-tetrahydroquinoline (3.8 g) in tetrahydrofuran (100 ml) was added dropwise thereto. The temperature was raised gradually to the room temperature, the mixture was stirred for 2.5 hours. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane and dried, then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (8:1)]to give 8-(t-butyldimethylsilyloxymethyl)-4-methylene-1-ethyl-1,2,3,4tetrahydroquinoline (3.4 g).

Workup

  1. additionwas added dropwise
  2. temperatureThe temperature was raised to -20° C. over 30 minutes
  3. temperatureThe temperature was raised gradually to the room temperature
  4. stirringthe mixture was stirred for 2.5 hours
  5. extractionthe mixture was extracted with dichloromethane
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-e8e863aa9c914989af40b5d20b2b82e4
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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