Dimethyl Sulfoxide → 1-(2-Tetrahydropyranyloxy)-15-hexadecene

HRID 1112

반응식

HRID 1112 반응식
[H-].[Na+].N#N.[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=O.O.[CH3:29]S(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:29]

참가 물질

8

반응물 5

HCID 679Dimethyl Sulfoxide2회HCID 947NitrogenHCID 962WaterHCID 24758Sodium hydrideHCID 1969465715-(2-Tetrahydropyranyloxy)pentadecanal

생성물 1

HCID 110564361-(2-Tetrahydropyranyloxy)-15-hexadecene수율 46%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매

실험 절차

A 300-ml three-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 40 ml of dimethyl sulfoxide and 1.2 g (30 mmol) of 60% sodium hydride. The contents were stirred at 75° C. for 1.5 hours in an N2 atmosphere and then cooled to room temperature. To this mixture, a solution of 8.93 g (25 mmol) of methyltriphenylphosphonium bromide in 40 ml of dimethyl sulfoxide was added dropwise over 10 minutes. The resultant mixture was stirred further for 20 minutes at room temperature. To this mixture, a solution of 3.27 g (10 mmol) of 15-(2-tetrahydropyranyloxy)pentadecanal in 15 ml of THF was added dropwise over 5 minutes, followed by stirring further for 30 minutes. After completion of the reaction, the reaction mixture was added with water and subjected to extraction with hexane, followed by concentration under reduced pressure. Thereafter, the resultant residue was purified by flash column chromatography on silica gel, thereby obtaining 1.49 g (yield: 46%) of 1-(2-tetrahydropyranyloxy)-15-hexadecene.

후처리

  1. customA 300-ml three-necked flask equipped with a stirrer
  2. customAfter completion of the reaction
  3. extractionsubjected to extraction with hexane
  4. concentrationfollowed by concentration under reduced pressure
  5. customThereafter, the resultant residue was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-9575b1a855c84db398427cd5e89360d1
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723497

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