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

HRID 1112
Notes
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Reaction equation

HRID 1112 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents

2
HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9575b1a855c84db398427cd5e89360d1
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723497

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes