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

HRID 1701419노트

반응식

HRID 1701419 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6bb58f9f129b4cd296080a636dca04ed
출처 데이터셋
uspto-grants-1980_03
특허 번호
US04192953

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