Sodium borohydride → HCID 20358500, compound

HRID 2083403Notes

Reaction equation

HRID 2083403 reaction equation
[CH3:1][C:2]([C:4]1([CH3:19])[CH2:9][O:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[O:6][CH2:5]1)=[O:3].[BH4-].[Na+]>CO.O>[CH3:1][CH:2]([C:4]1([CH3:19])[CH2:9][O:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[O:6][CH2:5]1)[OH:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13005018HCID 13005018, compound

Product 1

HCID 20358500HCID 20358500, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-methyl-2-(m-nitrophenyl)1,3-dioxan-5-yl methyl ketone (9.0 g) in methanol (100 ml) was added a solution of sodium borohydride (4.5 g) in water (20 ml). The mixture was heated under reflux for 1 hour, methanol was removed in vacuo and the residue was extracted with ether (3 × 100 ml). The extracts were dried (Na2SO4) and concentrated and the residue was crystallised from diethyl ether as pale yellow crystals m.p. 97°, cis isomer.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. custommethanol was removed in vacuo
  4. extractionthe residue was extracted with ether (3 × 100 ml)
  5. dry with materialThe extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue was crystallised from diethyl ether as pale yellow crystals m.p. 97°, cis isomer

Sources & evidence

ORD record
ord-d8e5fcef41ff4c3cb8cf9def4f66e908
Source dataset
uspto-grants-1978_04
Patent number
US04085222

Reaction notes

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