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

HRID 2257320Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-90d8c947d70b4ecbb61735ac231a6974
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05656657

Reaction notes

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