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

HRID 1112

反応式

HRID 1112 の反応式
[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]

参加物

8

反応物 5

HCID 679Dimethyl Sulfoxide2 回HCID 947NitrogenHCID 962WaterHCID 24758Sodium hydrideHCID 1969465715-(2-Tetrahydropyranyloxy)pentadecanal

生成物 1

HCID 110564361-(2-Tetrahydropyranyloxy)-15-hexadecene収率 46%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9575b1a855c84db398427cd5e89360d1
出典データセット
uspto-grants-1998_03
特許番号
US05723497

関連ノート

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