2-Methylbutyltriphenylphosphonium bromide → HCID 53696590, compound

HRID 2260072Notes

Reaction equation

HRID 2260072 reaction equation
[Br-].[CH3:2][CH:3]([CH2:24][CH3:25])[CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])=O>O1CCCC1>[CH3:2][CH:3]([CH2:24][CH3:25])[CH:4]=[CH:26][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43]

Participants

4

Reactant 2

HCID 113504802-Methylbutyltriphenylphosphonium bromideHCID 13555230Methyl 16-oxohexadecanoate

Product 1

HCID 53696590HCID 53696590, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

13 gm of 2-methylbutyltriphenylphosphonium bromide was pulverized and dispersed into 130 ml of anhydrous tetrahydrofuran. To this was added 23.7 ml of 1.5M butyl lithium-hexane solution under a nitrogen atmosphere and the mixture was stirred for 30 minutes. To the solution was slowly added 8.4 gm of methyl 15-formylpentadecanoate which had been dissolved in 130 ml of anhydrous tetrahydrofuran in advance. After stirring for 3 hours, the solvent was evaporated. The crude crystals thus obtained were purified by flash column chromatography (chloroform:hexane=1:1) to obtain 5.3 gm of methyl 18-methyl-16-eicosenoate (yield: 51%). The product was submitted to the next step without purification.

Workup

  1. additionTo this was added 23.7 ml of 1.5M butyl lithium-hexane solution under a nitrogen atmosphere
  2. stirringAfter stirring for 3 hours
  3. customthe solvent was evaporated
  4. customThe crude crystals thus obtained
  5. customwere purified by flash column chromatography (chloroform:hexane=1:1)

Sources & evidence

ORD record
ord-0383ea56fc884336b7a3ba1d0c3402b8
Source dataset
uspto-grants-1995_12
Patent number
US05476649

Reaction notes

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