Ethanol → HCID 13826435, compound

HRID 1906925Notes

Reaction equation

HRID 1906925 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:13]=[C:12]([Cl:14])[C:11]2[CH2:10][CH2:9][C:8]([Cl:16])([Cl:15])[C:7](=[O:17])[C:6]=2[C:5]=1[CH2:18][CH2:19][C:20]([O-:22])=[O:21].[CH2:23](O)[CH3:24]>[BH4-].[Na+]>[OH:17][CH:7]1[C:6]2[C:5]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:4]([CH3:3])[CH:13]=[C:12]([Cl:14])[C:11]=2[CH2:10][CH2:9][C:8]1([Cl:16])[Cl:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 20211071HCID 20211071, compound

Product 1

HCID 13826435HCID 13826435, compound

Reagents, catalysts & solvents 1

HCID 4311764Sodium borohydrideCatalyst2×

Procedure

Sodium borohydride (0.19 g, 5.02 mmoles) was added to a solution of 3-(2-methyl-8-oxo-5,6,7,8-tetrahydro-4,7,7-trichloronaphthalen-1-yl)propanoate (7.38 g, 20.3 mmoles) in ethanol (60 ml) which had been cooled in an ice-water bath. The reaction was allowed to stir for 15 minutes. Tlc (silica-CH2Cl2) showed reaction not complete. Add 20 mg of sodium borohydride first stirred in the cold for 15 minutes. Repeat addition of 20 mg of sodium borohydride with 15 minutes stirring in the cold twice more at which time tlc showed reaction complete. The reaction was then partitioned between ether (150 ml) and water (300 ml). The water was extracted with ether two times. The combined ether extracts were washed with water two times, dried (MgSO4), filtered, and the solvent evaporated in vacuo to leave 7.25 g of title compound as a gum.

Workup

  1. temperaturehad been cooled in an ice-water bath
  2. customreaction not complete
  3. stirringfirst stirred in the cold for 15 minutes
  4. stirringstirring in the cold twice more at which time tlc
  5. customreaction complete
  6. customThe reaction was then partitioned between ether (150 ml) and water (300 ml)
  7. extractionThe water was extracted with ether two times
  8. washThe combined ether extracts were washed with water two times
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-19bb0feb1a224803b74632281dcd4159
Source dataset
uspto-grants-1987_03
Patent number
US04654363

Reaction notes

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