Sodium Chloride → HCID 15575060, compound

HRID 1155670Notes

Reaction equation

HRID 1155670 reaction equation
[BH4-].[Na+].[C:3]1([CH2:9][C:10]2[S:14][C:13]([CH:15]=[O:16])=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-].[Na+]>C(O)C>[C:3]1([CH2:9][C:10]2[S:14][C:13]([CH2:15][OH:16])=[CH:12][CH:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydride2×HCID 7017105HCID 7017105, compound

Product 1

HCID 15575060HCID 15575060, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride pellets, 5.6 grams (0.15 mole), were added portionwise during 0.5 hour to a stirred, cooled, solution of 30.0 grams (0.15 mole) of 5-(phenylmethyl)thiophene-2-carboxaldehyde in 400 ml of ethanol. Cooling was continued until the sodium borohydride had completely dissolved. The reaction mixture was then heated at reflux for 0.75 hour, cooled, and concentrated under reduced pressure to give a residual oil. The oil was slurried in ice-water saturated with sodium chloride, and the mixture was extracted with three portions of 150 ml each of chloroform. The extracts were combined, then dried with magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give a residual oil. The oil was distilled under reduced pressure using a Kugelrohr distilling system to give 22.5 grams of 5-(phenylmethyl)thiophene-2-methanol; b.p. 106° C./0.2 mm.

Workup

  1. temperaturecooled
  2. temperatureCooling
  3. dissolutionhad completely dissolved
  4. temperatureThe reaction mixture was then heated
  5. temperatureat reflux for 0.75 hour
  6. temperaturecooled
  7. concentrationconcentrated under reduced pressure
  8. customto give a residual oil
  9. extractionthe mixture was extracted with three portions of 150 ml each of chloroform
  10. dry with materialdried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under reduced pressure
  13. customto give a residual oil
  14. distillationThe oil was distilled under reduced pressure
  15. distillationdistilling system

Sources & evidence

ORD record
ord-6d10018d7fa74afba9102ab65bfd30ad
Source dataset
uspto-grants-1982_06
Patent number
US04332815

Reaction notes

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