Acetic Acid → 7-Formyl-3,11,15,19-tetramethyl-2,6,10,14,18-eicosapentaen-1-ol tetrahydropyranyl ether

HRID 1701422Notes

Reaction equation

HRID 1701422 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CO[CH:8]([O:27]C)[C:9](=O)[CH2:10][CH2:11][CH:12]=[C:13]([CH3:25])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22].[C:29]([OH:32])(=[O:31])[CH3:30]>O1CCCC1>[O:31]1[CH2:10][CH2:9][CH2:8][CH2:30][CH:29]1[O:32][CH2:1][CH:2]=[C:3]([CH3:4])[CH2:11][CH2:12][CH:13]=[C:9]([CH:8]=[O:27])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:25])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 53946054HCID 53946054, compoundHCID 178418339Butyllithium

Product 1

HCID 572809427-Formyl-3,11,15,19-tetramethyl-2,6,10,14,18-eicosapentaen-1-ol tetrahydropyranyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure stated in Example 2-(1), 5.8 g of (E)-4-methyl-6-(2'-tetrahydropyranyloxy)-4-hexen-1-yltriphenylphosphonium iodide was treated with n-butyllithium in 30 ml of anhydrous tetrahydrofuran. Then, the resultant was treated with 3.2 g of 1,1-dimethoxy-6,10,14-trimethyl-5,9,13-pentadecatrien-2-one prepared by the process stated in Referential example 7. The resulting oil was treated with 40 ml of 50% acetic acid to yield 4.2 g of 7-formyl-3,11,15,19-tetramethyl-2,6,10,14,18-eicosapentaen-1-ol tetrahydropyranyl ether. The product was reduced with 150 mg of sodium borohydride and treated with p-toluenesulfonic acid in methanol in the same manner as stated earlier, and purified by the silica gel column chromatography to yield 1.6 g of the desired product. This was a mixture of the (E,E,E,E), (E,Z,Z,E), (E,Z,E,E) and (E,E,Z,E) isomers.

Workup

  1. customprepared by the process

Sources & evidence

ORD record
ord-fbd7fb23055348589b4d2c5df0475b81
Source dataset
uspto-grants-1980_03
Patent number
US04192953

Reaction notes

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