Sodium Sulfate → HCID 86736671, compound

HRID 426699Notes

Reaction equation

HRID 426699 reaction equation
[F:1]/[C:2](=[C:8](/[CH3:19])\[CH:9]=[CH:10]\[C:11]1[C:15]([CH3:16])=[C:14]([CH3:17])[O:13][C:12]=1[CH3:18])/[C:3](OCC)=[O:4].[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[F:1]/[C:2](/[C:8](/[CH3:19])=[CH:9]/[CH2:10][C:11]1[C:15]([CH3:16])=[C:14]([CH3:17])[O:13][C:12]=1[CH3:18])=[CH:3]\[OH:4]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 12960838HCID 12960838, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 86736671HCID 86736671, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-45 °C

Procedure

A solution of crude ethyl 2Z,4E-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-furyl)pentadienoate in ether was stirred under argon and cooled to -45° C. Diisobutylaluminum hydride (DIBAH) (112 mmol) was added slowly until no starting material remained. Five ml. of a saturated solution of sodium sulfate was added at -10° C. and the mixture was allowed to warm to 30° C. for a completion of hydrolysis. Filtration through Celite and evaporation gave 12 g. of 2Z,4E-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-furyl)pentadien-1-ol which was carried on to the next step without further purification.

Workup

  1. temperatureto warm to 30° C. for a completion of hydrolysis
  2. filtrationFiltration
  3. customthrough Celite and evaporation
  4. customgave 12 g
  5. customof 2Z,4E-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-furyl)pentadien-1-ol which was carried on to the next step without further purification

Sources & evidence

ORD record
ord-05e63e2a3b134883b6a78cbd6b84a387
Source dataset
uspto-grants-1979_10
Patent number
US04171318

Reaction notes

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