Methanol → HCID 23349109, compound

HRID 1855802Notes

Reaction equation

HRID 1855802 reaction equation
C([O:3][C:4](=O)/[CH:5]=[C:6](\[CH3:21])/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:20])/[CH:11]=[CH:12]/[C:13]1[C:17]([CH3:18])=[CH:16][O:15][C:14]=1[CH3:19])C.[H-].C([Al+]CC(C)C)C(C)C.CO.S([O-])([O-])(=O)=O.[Mg+2]>CCOCC>[CH3:21]/[C:6](/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:20])/[CH:11]=[CH:12]/[C:13]1[C:17]([CH3:18])=[CH:16][O:15][C:14]=1[CH3:19])=[CH:5]\[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21225700DiisobutylaluminumhydrideHCID 86737137HCID 86737137, compound

Product 1

HCID 23349109HCID 23349109, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(E,E,E,E)-3,7-dimethyl-9-(2,4-dimethyl-3-furyl)-2,4,6,8-nonatetraenoic acid ethyl ester (6 g.) in ether (25 ml.) was added to a solution of diisobutyl aluminum hydride (38 ml.; 25% by volume in hexane) at -40° and stirred for 30 minutes at room temperature. Aqueous methanol (1:1 parts by volume; 1.6 ml.) was added. The mixture was then carefully warmed to room temperature and then treated with anhydrous magnesium sulfate. The solids were filtered off and the solvents were removed to give (E,E,E,E)-3,7-dimethyl-9-(2,4,-dimethyl-3-furyl)-2,4,6,8-nonatetraenol as an oil. The pmr spectrum showed the complete absence of ester or aldehyde functions.

Workup

  1. temperatureThe mixture was then carefully warmed to room temperature
  2. filtrationThe solids were filtered off
  3. customthe solvents were removed

Sources & evidence

ORD record
ord-45e23635c8d646b7b42bc71ed14e31b1
Source dataset
uspto-grants-1980_08
Patent number
US04216312

Reaction notes

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