Sodium borohydride → HCID 14537114, compound

HRID 232406Notes

Reaction equation

HRID 232406 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)=[O:2].[BH4-].[Na+]>CO>[CH3:17][O:16][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[C:6]([CH2:5][CH2:4][CH2:3][CH2:1][OH:2])[CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14537113HCID 14537113, compound

Product 1

HCID 14537114HCID 14537114, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The starting 2-(3-formylpropyl)-4-methoxy-1-[(tetrahydro-2H-pyran-2-yl)-oxy]naphthalene (0.587 g) is dissolved in 5 ml methanol. This solution is placed under a nitrogen atmosphere and then cooled to 0°-5° C. and solid sodium borohydride (0.10 g) is added in one portion. Vigorous gas evolution ensues and after stirring for 30 min TLC analysis indicates the reduction is complete. The reaction is quenched with saturated aqueous ammonium chloride and then poured into water. The pH is adjusted to 2--3 (10% aqueous sodium bisulfate) and the mixture extracted with ether. The pH of the aqueous phase is raised to 7 (saturated aqueous sodium bicarbonate), excess solid sodium chloride is added and the mixture reequilibrated. The organic extract is dried with magnesium sulfate, filtered and concentrated to give the crude product as an orange colored oil.

Workup

  1. temperaturecooled to 0°-5° C.
  2. customThe reaction is quenched with saturated aqueous ammonium chloride
  3. additionpoured into water
  4. extractionthe mixture extracted with ether
  5. temperatureThe pH of the aqueous phase is raised to 7 (saturated aqueous sodium bicarbonate), excess solid sodium chloride
  6. additionis added
  7. extractionThe organic extract
  8. dry with materialis dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-365bf1956f6441a593df1d8ad60e0bb0
Source dataset
uspto-grants-1989_07
Patent number
US04851586

Reaction notes

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