p-Toluenesulfonic acid → (E,E,E)-7-Formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol

HRID 1701419ノート

反応式

HRID 1701419 の反応式
O1CCCCC1[O:7][CH2:8][CH:9]=[C:10]([CH3:28])[CH2:11][CH2:12][CH:13]=[C:14]([CH:26]=[O:27])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[CH:26](/[C:14](/[CH2:15][CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:13]/[CH2:12][CH2:11]/[C:10](/[CH3:28])=[CH:9]/[CH2:8][OH:7])=[O:27]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 569911137-Formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol tetrahydropyranyl ether

生成物 1

HCID 86735217(E,E,E)-7-Formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In 100 ml of methanol was dissolved 10.0 g of 7-formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol tetrahydropyranyl ether prepared in Example 2-(1), and to this solution was added 100 mg of p-toluenesulfonic acid. The mixture was allowed to stand overnight at room temperature and neutralized with an aqueous sodium hydrogencarbonate solution. The methanol was distilled off, and the residue was extracted with ether. (E,E,E)-7-Formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol obtained from the ethereal layer was dissolved in 60 ml of ethanol. After addition of 5.5 g of sodium borohydride under ice-cooling, the solution was vigorously stirred for 2 hours. The mixture was then treated with dilute acetic acid and, after addition of water, extracted with ether. The oil obtained from the ethereal layer was purified by the silica gel column chromatography, yielding 6.6 g of the desired (E,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol.

後処理

  1. distillationThe methanol was distilled off
  2. extractionthe residue was extracted with ether

出典と根拠

ORDレコード
ord-6bb58f9f129b4cd296080a636dca04ed
出典データセット
uspto-grants-1980_03
特許番号
US04192953

反応ノート

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