Hydrochloric Acid → HCID 20358241, compound

HRID 2083216Notes

Reaction equation

HRID 2083216 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH:14]([OH:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20358233HCID 20358233, compound

Product 1

HCID 20358241HCID 20358241, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 3.13 g (0.010 mole) of 4-[5-(3,4-dichlorophenyl)-2-furanyl]-4-oxobutanoic acid and 50 ml of 95% dioxane/water was treated portionwise with 0.95 g (0.025 mole) of NaBH4 while maintaining the temperature below 20° by means of an ice bath. The resulting near solution was allowed to stand overnight at room temperature and was then added to ice/water. After acidifying with 20% hydrochloric acid, the resulting oily mixture was extracted with ether and the ethereal extract dried over MgSO4. The ether was removed on a Calab evaporator yielding 3 g (96%) of product as a residual oil.

Workup

  1. temperaturewhile maintaining the temperature below 20° by means of an ice bath
  2. extractionthe resulting oily mixture was extracted with ether
  3. extractionthe ethereal extract
  4. dry with materialdried over MgSO4
  5. customThe ether was removed on a Calab evaporator

Sources & evidence

ORD record
ord-4687cd408f58462aab27a7712858a392
Source dataset
uspto-grants-1978_04
Patent number
US04085118

Reaction notes

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