Diisopropyl Ether → HCID 19603379, compound

HRID 1604583Notes

Reaction equation

HRID 1604583 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[CH:20]=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(OC(C)C)(C)C>CO.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[CH2:20][OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 4311764Sodium borohydrideHCID 19603443HCID 19603443, compound

Product 1

HCID 19603379HCID 19603379, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 8-benzyloxy-4-formyl-2-methylquinoline (300 mg) in a mixture of methanol (3 ml) and tetrahydrofuran (2 ml) was added sodium borohydride (20.6 mg) portionwise in an ice bath. The suspension was stirred for half an hour, then quenched with saturated sodium chloride. The mixture was extracted with chloroform and the organic layer was dried over anhydrous magnesium sulfate. After being concentrated in vacuo the residue was chromatographed on silica gel eluting with ethyl acetate-n-hexane to give an amorphous solid which was solidified with diisopropyl ether to afford 8-benzyloxy-4-hydroxymethyl-2-methylquinoline (250 mg) as a colorless solid.

Workup

  1. customquenched with saturated sodium chloride
  2. extractionThe mixture was extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationAfter being concentrated in vacuo the residue
  5. customwas chromatographed on silica gel eluting with ethyl acetate-n-hexane
  6. customto give an amorphous solid which

Sources & evidence

ORD record
ord-93d4159f5be34520aa195bc5d67c7fcc
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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