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Toluene → HCID 22841014, 화합물

HRID 329514
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HRID 329514 반응식
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([OH:16])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[OH-].[K+].C1(C)C=CC=CC=1>O>[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:15]([O:16][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1140TolueneHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 22841016HCID 22841016, 화합물

생성물 1

HCID 22841014HCID 22841014, 화합물

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of 1.037 g of dl-cis-2-benzyloxymethyltetrahydropyran-3-ol (prepared as described in Preparation 33), 1.709 g of hexadecyl bromide, 0.77 g of potassium hydroxide and 15 ml of toluene was heated, with stirring, at 120° C. for 10 hours. At the end of this time, the reaction mixture was cooled and then poured into water. The aqueous layer was extracted twice with diethyl ether. The organic layer and the extracts were combined, washed with water, dried over anhydrous magnesium sulfate and condensed by evaporation under reduced pressure. The resulting oily residue (3.3 g) was subjected to column chromatography through 50 g of silica gel. The fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane gave 1.455 g of the title compound as a colorless oily substance.

후처리

  1. temperaturewas heated
  2. temperatureAt the end of this time, the reaction mixture was cooled
  3. extractionThe aqueous layer was extracted twice with diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate and condensed by evaporation under reduced pressure
  6. washThe fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane

출처 및 근거

ORD 기록
ord-f727afdebb8241899a9b99fb021713ec
출처 데이터셋
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04891363

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