Acetic Anhydride → HCID 22161803, compound

HRID 1088808Notes

Reaction equation

HRID 1088808 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][CH:15]2[CH2:22][OH:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[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][CH:15]2[CH2:22][O:23][C:24](=[O:26])[CH3:25])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22161767HCID 22161767, compound

Product 1

HCID 22161803HCID 22161803, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 8-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (1.98 g) in pyridine (5 ml), acetic anhydride was added dropwise with stirring under ice-cooling and the mixture was stirred for 2 hours at room temperature. Pyridine was distilled off under reduced pressure, and the resultant residue was extracted with dichloromethane. After washing with a saturated aqueous solution of copper sulfate and with water in this order, the mixture was dried and the solvent was distilled off under reduced pressure to give 8-t-butyldimethylsilyloxymethyl-4-acetyloxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (2.23 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. distillationPyridine was distilled off under reduced pressure
  4. extractionthe resultant residue was extracted with dichloromethane
  5. washAfter washing with a saturated aqueous solution of copper sulfate and with water in this order
  6. customthe mixture was dried
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-eb43a212498e42418b51f5fbf2beee62
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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