Hydrochloric Acid → HCID 15391779, compound

HRID 428167Notes

Reaction equation

HRID 428167 reaction equation
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][CH2:2]1)[O:11][CH2:10][C:9]([CH:15]=[O:16])=[CH:8]3.[BH4-].[Na+].Cl>C(O)C>[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][CH2:2]1)[O:11][CH2:10][C:9]([CH2:15][OH:16])=[CH:8]3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15391778HCID 15391778, compound

Product 1

HCID 15391779HCID 15391779, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.18 g (10 mmol) of the aldehyde obtained in Step C are dissolved in 25 ml of anhydrous ethanol and then 0.38 g (10 mmol) of sodium borohydride is added to the medium. After 15 minutes of stirring, the solvent is evaporated in vacuo; the residue obtained is then acidified with a 1N hydrochloric acid solution. The aqueous phase is extracted with dichloromethane; the organic phase is then dried over magnesium sulphate and then concentrated under reduced pressure. The crude product is passed over a silica column (eluant:petroleum ether/ethyl acetate:70/30 then 50/50) to yield the title alcohol in the form of a clear syrup.

Workup

  1. customthe solvent is evaporated in vacuo
  2. customthe residue obtained
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. dry with materialthe organic phase is then dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db7ebe697ea248e88bc67c4b6e26256f
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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