Water → HCID 53818560, compound

HRID 1579078Notes

Reaction equation

HRID 1579078 reaction equation
O.[O:2]1CCCC1.[CH3:7][C:8]([CH:14]=[CH:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:9][C:10](=[O:13])[CH2:11][CH3:12].[BH4-].[Na+]>[OH-].[Na+]>[OH:2][C:21]([CH3:22])([CH3:23])[CH2:20][CH2:19][CH2:18][CH:17]([CH3:24])[CH2:16][CH:15]=[CH:14][C:8]([CH3:7])=[CH:9][C:10](=[O:13])[CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 54521383HCID 54521383, compound

Product 1

HCID 53818560HCID 53818560, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a mixture of 1.9 g. of mercuric acetate, 6 ml. of water and 20 ml. of tetrahydrofuran is added 1.49 g. of 5,9,13-trimethyltetradeca-4,6,12-trien-3-one slowly. After addition is complete, the reaction mixture is stirred for about 20 minutes. The mixture is cooled to about 0° and 6 ml. of aqueous sodium hydroxide (3 molar) is added followed by 0.49 g. of sodium borohydride in aqueous sodium hydroxide (about 3 molar). The mixture is stirred for about 30 minutes. The mixture is then decanted, concentrated, diluted with water and then extracted with ether. The ethereal extract is washed with water, dried over magnesium sulfate and the product chromatographed on silica to yield 13-hydroxy-5,9,13-trimethyltetradeca-4,6-dien-3-one.

Workup

  1. additionTo a mixture of 1.9 g
  2. additionAfter addition
  3. temperatureThe mixture is cooled to about 0°
  4. stirringThe mixture is stirred for about 30 minutes
  5. customThe mixture is then decanted
  6. concentrationconcentrated
  7. additiondiluted with water
  8. extractionextracted with ether
  9. extractionThe ethereal extract
  10. washis washed with water
  11. dry with materialdried over magnesium sulfate
  12. customthe product chromatographed on silica

Sources & evidence

ORD record
ord-9b1d12bf224d4a4a980691aa1be0c139
Source dataset
uspto-grants-1976_02
Patent number
US03940444

Reaction notes

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