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

HRID 1440852
Notes
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Reaction equation

HRID 1440852 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-7d868f7e2847449ea158726d80ae6315
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05500425

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes