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Potassium Hydroxide → 5-Hydroxymethyl-3-(N-isopropyl-N-propylamino)chroman

HRID 37663
Notes
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Reaction equation

HRID 37663 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH:8]([N:15]([CH:19]([CH3:21])[CH3:20])[CH2:16][CH2:17][CH3:18])[CH2:9][O:10]2)=O.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.CCCCCC>[OH:2][CH2:3][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH:8]([N:15]([CH:19]([CH3:20])[CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:9][O:10]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 190281055-Methyloxycarbonyl-3-(N-isopropyl-N-propylamino)chromanHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 190281675-Hydroxymethyl-3-(N-isopropyl-N-propylamino)chromanYield 97%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

5-Methyloxycarbonyl-3-(N-isopropyl-N-propylamino)chroman (0.69 g, 2.36 mmol) was dissolved in 25 mL of dry methylene chloride and cooled to -78° C. A 1M solution of diisobutylaluminum hydride in hexane (6.6 mL) was added dropwise and the reaction was allowed to warm to room temperature for 50 min. A 1M solution of KOH was added dropwise and then the reaction was put into the refrigerator over night. The solution was poured through a pad of Na2SO4, dried (Na2SO4), filtered and the solvent removed in vacuo to give 0.60 g (97% yield) of the title compound as a clear oil.

Workup

  1. temperatureto warm to room temperature for 50 min
  2. waitthe reaction was put into the refrigerator over night
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cea37720bb5047429222fd3c9abed28a
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05420151

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes